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(11) | EP 3 277 674 B1 |
(12) | EUROPEAN PATENT SPECIFICATION |
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(54) |
TRIAZOL DERIVATIVES AS FUNGICIDES TRIAZOLDERIVATE ALS FUNGIZIDE DÉRIVÉS DE TRIAZOLE COMME FUNGICIDES |
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Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). |
wherein X1, X2, X3, X4 or X5 have the same definition as given for formula (I) above. X1, X2, X3, X4 or X5 preferably represent hydrogen or halogen, wherein at least one of X1, X2, X3, X4 or X5, being present in the heterocycle, is different from hydrogen.
Q more preferably represents a substituted 3-pyridyl or 4-pyridyl of formula (Q-I-1) to (Q-I-2)
wherein X1, X2, X3, X4 or X5 have the same definition as given for formula (I) above. X1, X2, X3, X4 or X5 preferably represent hydrogen or halogen, wherein at least one of X1, X2, X3, X4 or X5, being present in the heterocycle, is different from hydrogen.
Îllustration of the processes and intermediates
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Y | = -H or -OH |
Z | = halogen, -OSO2-C1-C8-alkyl, -OSO2-aryl, -OP(O)(O-C1-C8-alkyl)2 or -OP(O)(O-aryl)2, preferably Cl or Br |
A | = halogen, preferably Cl |
E | = -O-C1-C8-alkyl, preferably -O-methyl, -O-ethyl; -O-aryl; -S-C1-C8-alkyl; -S-aryl; -NHRa; -NRaRb; Ra: is aryl, C1-C8-alkyl or C3-C7-cycloalkyl, Rb: is C1-C8-alkyl or C1-C8-alkyloxy, preferably -NMe2, -NMeOMe; or heterocyclic leaving groups, such as imidazole, triazole and hydroxybenzotriazole. |
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A = halogen, preferably Cl | |
E = -O-C1-C8-alkyl, preferably -O-methyl, -O-ethyl; -O-aryl; -S-C1-C8-alkyl; -S-aryl; -NHRa; -NRaRb; Ra: is aryl, C1-C8-alkyl or C3-C7-cycloalkyl, Rb: is C1-C8-alkyl or C1-C8-alkyloxy, preferably -NMe2, -NMeOMe; or heterocyclic leaving groups, such as imidazole, triazole and hydroxybenzotriazole. |
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Z = halogen, preferably Cl or Br | |
n = 0 or 1 | |
M = Li, MgZM, ZnZM, Si(C1-C8-alkyl)3 or Sn(C1-C8-alkyl)3 | |
ZM = halogen or hydroxyl, preferably Cl or Br |
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G = halogen or hydrogen | |
A = halogen, O-SO2-C1-C8-alkyl or O-SO2-aryl, preferably Cl or Br |
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A = halogen, O-SO2-C1-C8-alkyl or O-SO2-aryl, preferably Cl or Br |
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A = halogen, O-SO2-C1-C8-alkyl or O-SO2-aryl, preferably Cl or Br |
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G = halogen or hydrogen |
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G = halogen or hydrogen |
General
Methods and uses
Plants
Pathogens
diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis; Podosphaera species, for example Podosphaera leucotricha; Sphaerotheca species, for example Sphaerotheca fuliginea; Uncinula species, for example Uncinula necator;
diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis; Uromyces species, for example Uromyces appendiculatus;
diseases caused by pathogens from the group of the Oomycetes, for example Albugo species, for example Albugo candida; Bremia species, for example Bremia lactucae; Peronospora species, for example Peronospora pisi or P. brassicae; Phytophthora species, for example Phytophthora infestans; Plasmopara species, for example Plasmopara viticola; Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, for example Pythium ultimum;
leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium cucumerinum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, for example Colletotrichum lindemuthanium; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthe citri; Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species, for example Gloeosporium laeticolor; Glomerella species, for example Glomerella cingulata; Guignardia species, for example Guignardia bidwelli; Leptosphaeria species, for example Leptosphaeria maculans; Magnaporthe species, for example Magnaporthe grisea; Microdochium species, for example Microdochium nivale; Mycosphaerella species, for example Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis; Phaeosphaeria species, for example Phaeosphaeria nodorum; Pyrenophora species, for example Pyrenophora teres or Pyrenophora tritici repentis; Ramularia species, for example Ramularia collo-cygni or Ramularia areola; Rhynchosporium species, for example Rhynchosporium secalis; Septoria species, for example Septoria apii or Septoria lycopersici; Stagonospora species, for example Stagonospora nodorum; Typhula species, for example Typhula incarnata; Venturia species, for example Venturia inaequalis;
root and stem diseases caused, for example, by Corticium species, for example Corticium graminearum; Fusarium species, for example Fusarium oxysporum; Gaeumannomyces species, for example Gaeumannomyces graminis; Plasmodiophora species, for example Plasmodiophora brassicae; Rhizoctonia species, for example Rhizoctonia solani; Sarocladium species, for example Sarocladium oryzae; Sclerotium species, for example Sclerotium oryzae; Tapesia species, for example Tapesia acuformis; Thielaviopsis species, for example Thielaviopsis basicola;
ear and panicle diseases (including corn cobs) caused, for example, by Alternaria species, for example Alternaria spp.; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium cladosporioides; Claviceps species, for example Claviceps purpurea; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Monographella species, for example Monographella nivalis; Stagnospora species, for example Stagnospora nodorum;
diseases caused by smut fungi, for example Sphacelotheca species, for example Sphacelotheca reiliana; Tilletia species, for example Tilletia caries or Tilletia controversa; Urocystis species, for example Urocystis occulta; Ustilago species, for example Ustilago nuda;
fruit rot caused, for example, by Aspergillus species, for example Aspergillus flavus; Botrytis species, for example Botrytis cinerea; Penicillium species, for example Penicillium expansum or Penicillium purpurogenum; Rhizopus species, for example Rhizopus stolonifer; Sclerotinia species, for example Sclerotinia sclerotiorum; Verticilium species, for example Verticilium alboatrum;
seed- and soil-borne rot and wilt diseases, and also diseases of seedlings, caused, for example, by Alternaria species, for example Alternaria brassicicola; Aphanomyces species, for example Aphanomyces euteiches; Ascochyta species, for example Ascochyta lentis; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichum species, for example Colletotrichum coccodes; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Macrophomina species, for example Macrophomina phaseolina; Microdochium species, for example Microdochium nivale; Monographella species, for example Monographella nivalis; Penicillium species, for example Penicillium expansum; Phoma species, for example Phoma lingam; Phomopsis species, for example Phomopsis sojae; Phytophthora species, for example Phytophthora cactorum; Pyrenophora species, for example Pyrenophora graminea; Pyricularia species, for example Pyricularia oryzae; Pythium species, for example Pythium ultimum; Rhizoctonia species, for example Rhizoctonia solani; Rhizopus species, for example Rhizopus oryzae; Sclerotium species, for example Sclerotium rolfsii; Septoria species, for example Septoria nodorum; Typhula species, for example Typhula incarnata; Verticillium species, for example Verticillium dahliae;
cancers, galls and witches' broom caused, for example, by Nectria species, for example Nectria galligena;
wilt diseases caused, for example, by Monilinia species, for example Monilinia laxa;
deformations of leaves, flowers and fruits caused, for example, by Exobasidium species, for example Exobasidium vexans; Taphrina species, for example Taphrina deformans;
degenerative diseases in woody plants, caused, for example, by Esca species, for example Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; Ganoderma species, for example Ganoderma boninense;
diseases of flowers and seeds caused, for example, by Botrytis species, for example Botrytis cinerea;
diseases of plant tubers caused, for example, by Rhizoctonia species, for example Rhizoctonia solani; Helminthosporium species, for example Helminthosporium solani;
diseases caused by bacterial pathogens, for example Xanthomonas species, for example Xanthomonas campestris pv. oryzae; Pseudomonas species, for example Pseudomonas syringae pv. lachrymans; Erwinia species, for example Erwinia amylovora.
Plant Growth Regulation
improved processability relating to size distribution (kernel, fruit, etc.), homogenous riping, grain moisture, better milling, better vinification, better brewing, increased juice yield, harvestability, digestibility, sedimentation value, falling number, pod stability, storage stability, improved fiber length/strength/uniformity, increase of milk and/or meet quality of silage fed animals, adaption to cooking and frying;
further comprising improved marketability relating to improved fruit/grain quality, size distribution (kernel, fruit, etc.), increased storage / shelf-life, firmness / softness, taste (aroma, texture, etc.), grade (size, shape, number of berries, etc.), number of berries/fruits per bunch, crispness, freshness, coverage with wax, frequency of physiological disorders, colour, etc.;
further comprising increased desired ingredients such as e.g. protein content, fatty acids, oil content, oil quality, aminoacid composition, sugar content, acid content (pH), sugar/acid ratio (Brix), polyphenols, starch content, nutritional quality, gluten content/index, energy content, taste, etc.;
and further comprising decreased undesired ingredients such as e.g. less mycotoxines, less aflatoxines, geosmin level, phenolic aromas, lacchase, polyphenol oxidases and peroxidases, nitrate content etc.
Resistance Induction /Plant Health and other effects
Mycotoxins
Material Protection
Formulations
Mixtures
Seed Treatment
Antimycotic Effects
GMO
Application Rates
Examples
Preparation examples
Preparation of compounds of the formula (I) according to process J:
Example 1: Preparation of 1-(2-chloro-3-fluoro-4-pyridyl)-2-(2,4-difluorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-ol (I-08)
Preparation of compounds of the formula (I) according to process H:
Example 2: Preparation of 2-(4-chloro-2-fluoro-phenyl)-1-(2-chloro-3-pyridyl)-3-(1,2,4-triazol-1-yl)propan-2-ol (I-29)
Preparation of compounds of the formula (XII) according to process D:
Example 3: Preparation of 2-chloro-3-[[2-(4-chloro-2-fluoro-phenyl)oxiran-2-yl]methyl]pyridine (XII-1)
Ex N° | R1 | R2 | Q | LogP |
I-01 | 4-phenoxyphenyl | H | 3-chloropyridin-4-yl | 2,46[a] |
I-02 | biphenyl-4-yl | H | 3-chloropyridin-4-yl | 2,46[a] |
I-03 | 4-phenoxyphenyl | H | 3-fluoropyridin-4-yl | 2,13[a] |
I-04 | biphenyl-4-yl | H | 3-fluoropyridin-4-yl | 2,13[a] |
I-05 | 4-fluorophenyl | H | 2-chloropyridin-4-yl | 1,69[a] |
I-06 | 4-(4-chlorophenoxy)phenyl | H | 3-chloropyridin-4-yl | 2,90[a] |
I-07 | 2-chlorophenyl | H | 2-chloro-3-fluoropyridin-4-yl | 2,27[a] |
I-08(*) | 2,4-difluorophenyl | H | 2-chloro-3-fluoropyridin-4-yl | 2,14[a] |
I-09 | 2,4-dichlorophenyl | H | 2-chloro-3-fluoropyridin-4-yl | 2,69[a] |
I-10 | 4-chlorophenyl | H | 2-chloro-3-fluoropyridin-4-yl | 2,23[a] |
I-11 | 4-chlorophenyl | H | 3-chloropyridin-4-yl | 1,86[a] |
I-12 | 2-chlorophenyl | H | 3-chloropyridin-4-yl | 1,93[a]; 1,97[b] |
I-13 | 4-fluorophenyl | H | 3-fluoropyridin-4-yl | 1,26[a] |
I-14 | phenyl | H | 5-chloro-2-fluoropyridin-4-yl | 2,02[a] |
I-15 | 4-fluorophenyl | H | 5-chloro-2-fluoropyridin-4-yl | 2,12[a] |
I-16 | 4-(trifluoromethyl)phenyl | H | 2-chloropyridin-3-yl | 2,22[a] |
I-17 | 3-chlorophenyl | H | 2-chloropyridin-3-yl | 1,97[a] |
I-18 | 4- fluorophenyl | H | 3-chloropyridin-4-yl | 1,57[a] |
I-19 | 4-(2,4-difluorophenoxy)phenyl | H | 3-chloropyridin-4-yl | 2,57[a] |
I-20 | 4-(2,4-difluorophenoxy)phenyl | H | 3-fluoropyridin-4-yl | 2,27[a] |
I-21 | 3-chlorophenyl | H | 3-chloropyridin-4-yl | 1,85[a]; 1,90[b] |
I-22 | 3-phenoxyphenyl | H | 3-chloropyridin-4-yl | 2,43[a]; 2,42[b] |
I-23 | 4-fluorophenyl | H | 2-chloro-3-fluoropyridin-4-yl | 1,91[a] |
I-24 | 4-phenoxyphenyl | H | 2-chloropyridin-4-yl | 2,57[a] |
I-25 | 4-(2,4-difluorophenoxy)phenyl | H | 2-chloropyridin-4-yl | 2,69[a] |
I-26 | biphenyl-4-yl | H | 2-chloro-5-fluoropyridin-4-yl | 2,88[a] |
I-27 | biphenyl-4-yl | H | 5-chloro-2-fluoropyridin-4-yl | 3,02[a] |
I-28 | 4-chlorophenyl | H | 5-chloro-2-fluoropyridin-4-yl | 2,43[a] |
I-29 | 4-chloro-2-fluorophenyl | H | 2-chloropyridin-3-yl | 2,15[a] |
I-30 | 2,4-difluorophenyl | H | 3-chloropyridin-4-yl | 1,76[a] |
I-31 | 4-chlorophenyl | H | 3-fluoropyridin-4-yl | 1,54[a] |
I-32 | 4-fluorophenyl | H | 2-chloro-5-fluoropyridin-4-yl | 1,96[a] |
I-33 | phenyl | H | 3-chloropyridin-4-yl | 1,48[a]; 1,59[b] |
I-34 | 4-phenoxyphenyl | H | 5-chloro-2-fluoropyridin-4-yl | 3,02[a] |
I-35 | 4-cyanophenyl | H | 2-chloropyridin-3-yl | 1,47[a] |
I-36 | phenyl | H | 3-fluoropyridin-4-yl | 1,13[a] |
I-37 | phenyl | H | 2-chloropyridin-4-yl | 1,60[a] |
I-38 | 4-(3-tert-butyl-l,2,4-oxadiazol-5-yl)phenyl | H | 3-chloropyridin-4-yl | 2,65[a] |
I-39 | biphenyl-4-yl | H | 2-chloropyridin-4-yl | 2,57[a] |
I-40 | 4-chlorophenyl | H | 2-chloro-5-fluoropyridin-4-yl | 2,27[a] |
I-41 | 2,4-difluorophenyl | H | 5-chloro-2-fluoropyridin-4-yl | 2,35[a] |
I-42 | 2,4-dichlorophenyl | H | 3-chloropyridin-4-yl | 2,38[a] |
I-43 | 2,4-difluorophenyl | H | 3-fluoropyridin-4-yl | 1,47[a] |
I-44 | 2,4-difluorophenyl | H | 2-chloropyridin-4-yl | 1,86[a] |
I-45 | 2,4-difluorophenyl | H | 2-chloro-5-fluoropyridin-4-yl | 2,13[a] |
I-46 | 4-phenoxyphenyl | H | 2-chloro-3-fluoropyridin-4-yl | 2,84[a] |
I-47 | 4-chlorophenyl | H | 2-chloropyridin-4-yl | 1,96[a] |
I-48 | phenyl | H | 2-chloro-5-fluoropyridin-4-yl | 1,86[a] |
I-49 | phenyl | H | 2-chloro-3-fluoropyridin-4-yl | 1,84[a] |
I-50 | 2,4-dichlorophenyl | H | 2-chloropyridin-4-yl | 2,42[a] |
I-51 | phenyl | H | 2-chloropyridin-3-yl | 1,61[a] |
I-52 | 4-chlorophenyl | H | 2 -chloropyridin-3 -yl | 1,99[a] |
I-53 | 2,4-dichlorophenyl | H | 3-fluoropyridin-4-yl | 2,00[a] |
I-54 | 4-(2,4-difluorophenoxy)phenyl | H | 5-chloro-2-fluoropyridin-4-yl | 3,02[a] |
I-55(*) | 2,4-difluorophenyl | H | 2-chloro-3-fluoropyridin-4-yl | 2,21[a] |
I-56(*) | 2,4-difluorophenyl | H | 2-chloro-3-fluoropyridin-4-yl | 2,21[a] |
I-57 | 2,4-difluorophenyl | methyl | 2-chloro-3-fluoropyridin-4-yl | 2,47[a] |
Optical rotation Concentration c is expressed in g/100 mL (*) Ex I-55 and 1-56 are the 2 enantiomers of Ex I-08 Ex I-55: Optical rotation: + 3.1 (c = 1,129; DCM, 25°C) Ex I-56: Optical rotation: - 3.4 (c = 1,160; DCM, 25°C) |
Ex N° | R1 | Q | LogP |
XII-1 | 4-chloro-2- fluorophenyl | 2-chloropyridin-3-yl | 3,31[a] |
XII-2 | 4-chlorophenyl | 3-fluoropyridin-4-yl | 2,65[a] |
XII-3 | 2,4-dichlorophenyl | 3-fluoropyridin-4-yl | 3,19[a] |
XII-4 | 4-fluorophenyl | 3-fluoropyridin-4-yl | 2,23[a] |
XII-5 | 4-(2,4-difluorophenoxy)phenyl | 3-fluoropyridin-4-yl | 3,37[a] |
XII-6 | 2,4-difluorophenyl | 3-fluoropyridin-4-yl | 2,38[a] |
XII-7 | 4-phenoxyphenyl | 3-fluoropyridin-4-yl | 3,37[a] |
XII-8 | biphenyl-4-yl | 3-fluoropyridin-4-yl | 3,37[a] |
XII-9 | 4-phenoxyphenyl | 2-chloropyridin-4-yl | 3,37[a] |
XII-10 | 2,4-dichlorophenyl | 2-chloropyridin-4-yl | 3,85[a] |
XII-11 | 2,4-difluorophenyl | 2-chloropyridin-4-yl | 2,93[a] |
XII-12 | 4-(2,4-difluorophenoxy)phenyl | 2-chloropyridin-4-yl | 3,85[a] |
XII-13 | biphenyl-4-yl | 2-chloropyridin-4-yl | 3,89[a] |
XII-14 | 4-fluorophenyl | 2-chloropyridin-4-yl | 2,76[a] |
XII-15 | 4-chlorophenyl | 2-chloropyridin-4-yl | 3,19[a] |
XII-16 | 4-fluorophenyl | 2-chloro-5-fluoropyridin-4-yl | 3,15[a] |
XII-17 | 4-chlorophenyl | 2-chloro-5-fluoropyridin-4-yl | 3,56[a] |
XII-18 | 4-phenoxyphenyl | 2-chloro-5-fluoropyridin-4-yl | 4,23[a] |
XII-19 | 2,4-dichlorophenyl | 2-chloro-5-fluoropyridin-4-yl | 4,17[a] |
XII-20 | 2,4-difluorophenyl | 2-chloro-5-fluoropyridin-4-yl | 3,24[a] |
XII-21 | 4-(2, 4-difluorophenoxy)phenyl | 2-chloro-5-fluoropyridin-4-yl | 4,17[a] |
XII-22 | biphenyl-4-yl | 2-chloro-5-fluoropyridin-4-yl | 4,28[a] |
XII-23 | 3-chlorophenyl | 2-chloropyridin-3-yl | 3,24[a] |
XII-24 | 4-chlorophenyl | 2-chloropyridin-3-yl | 3,25[a] |
XII-25 | 4 -(trifluoromethyl)phenyl | 2-chloropyridin-3-yl | 3,46[a] |
XII-26 | 4-cyanophenyl | 2-chloropyridin-3-yl | 2,35[a] |
XII-27 | 4-fluorophenyl | 3-chloropyridin-4-yl | 2,65[a] |
XII-28 | biphenyl-4-yl | 3-chloropyridin-4-yl | 3,85[a] |
XII-29 | 2-chlorophenyl | 3-chloropyridin-4-yl | 3,02[a] |
XII-30 | 4-chlorophenyl | 3-chloropyridin-4-yl | 3,15[a] |
XII-31 | 2,4-dichlorophenyl | 3-chloropyridin-4-yl | 3,06[a] |
XII-32 | 4-phenoxyphenyl | 3-chloropyridin-4-yl | 3,80[a] |
XII-33 | 4-(2,4-difluorophenoxy)phenyl | 3-chloropyridin-4-yl | 3,80[a] |
XII-34 | 2,4-difluorophenyl | 3-chloropyridin-4-yl | 2,76[a] |
XII-35 | 2,4-difluorophenyl | 5-chloro-2-fluoropyridin-4-yl | 3,46[a] |
XII-36 | 2,4-dichlorophenyl | 5-chloro-2-fluoropyridin-4-yl | 4,45[a] |
XII-37 | 4-chlorophenyl | 5-chloro-2-fluoropyridin-4-yl | 3,85[a] |
XII-38 | 2-chlorophenyl | 5-chloro-2-fluoropyridin-4-yl | 3,80[a] |
XII-39 | 4-fluorophenyl | 5-chloro-2-fluoropyridin-4-yl | 3,37[a] |
XII-40 | 4-phenoxyphenyl | 5-chloro-2-fluoropyridin-4-yl | 4,57[a] |
XII-41 | 4-(2,4-difluorophenoxy)phenyl | 5-chloro-2-fluoropyridin-4-yl | 4,51[a] |
XII-42 | biphenyl-4-yl | 5-chloro-2-fluoropyridin-4-yl | 4,64[a] |
XII-43 | 4-chlorophenyl | 2-chloro-3-fluoropyridin-4-yl | 3,58[a] |
XII-44 | 4-(2,4-difluorophenoxy)phenyl | 2-chloro-3-fluoropyridin-4-yl | 4,20[a] |
XII-45 | biphenyl-4-yl | 2-chloro-3-fluoropyridin-4-yl | 4,25[a] |
XII-46 | 2,4-dichlorophenyl | 2-chloro-3-fluoropyridin-4-yl | 3,02[a] |
XII-47 | 2,4-difluorophenyl | 2-chloro-3-fluoropyridin-4-yl | 3,26[a] |
XII-48 | 4-phenoxyphenyl | 2-chloro-3-fluoropyridin-4-yl | 4,20[a] |
XII-49 | 2-chlorophenyl | 2-chloro-3-fluoropyridin-4-yl | 3,47[a] |
XII-50 | 4-fluorophenyl | 2-chloro-3-fluoropyridin-4-yl | 3,11[a] |
XII-51 | 4-phenoxyphenyl | 3,5-dichloropyridin-4-yl | 4,76[a] |
XII-52 | 4-(2,4-difluorophenoxy)phenyl | 3,5-dichloropyridin-4-yl | 4,70[a] |
XII-53 | biphenyl-4-yl | 3,5-dichloropyridin-4-yl | 4,89[a] |
XII-54 | 2,4-dichlorophenyl | 3,5-dichloropyridin-4-yl | 4,76[a] |
XII-55 | 2,4-difluorophenyl | 3,5-dichloropyridin-4-yl | 3,68[a] |
XII-56 | 4-fluorophenyl | 3,5-dichloropyridin-4-yl | 3,58[a] |
XII-57 | 4-chlorophenyl | 3,5-dichloropyridin-4-yl | 4,10[a] |
XII-58 | phenyl | 3,5-dichloropyridin-4-yl | 3,53[a] |
XII-59 | 2-chlorophenyl | 3,5-dichloropyridin-4-yl | 4,04[a] |
XII-60 | mesityl | 3-chloropyridin-4-yl | 4,15[a] |
XII-61 | 2,3-dichlorophenyl | 3-chloropyridin-4-yl | 3,53[a] |
XII-62 | 2,6-dichlorophenyl | 3-chloropyridin-4-yl | 3,02[a] |
XII-63 | 3-[(2-chlorobenzyl)oxy]phenyl | 3-chloropyridin-4-yl | 4,30[a] |
XII-64 | 4-[(2-chlorobenzyl)oxy]phenyl | 3-chloropyridin-4-yl | 4,30[a] |
XII-65 | 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl | 3-chloropyridin-4-yl | 4,25[a] |
XII-66 | 2,6-difluorophenyl | 3-chloropyridin-4-yl | 2,50[a] |
Measurement of LogP values was performed according to EEC directive 79/831 Annex V.A8
by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the
following methods: [a] LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). [b] LogP value is determined by measurement of LC-UV, in a neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). [c] LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% phosphoric acid and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). |
NMR-Peak lists
Example I-01: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.433 (11.0); 8.294 (7.1); 8.282 (16.0); 7.922 (13.5); 7.406 (0.8); 7.401 (4.9); 7.395 (1.8); 7.388 (1.1); 7.382 (7.1); 7.379 (6.7); 7.373 (1.1); 7.366 (2.3); 7.361 (6.3); 7.355 (1.8); 7.348 (8.6); 7.342 (2.8); 7.331 (3.0); 7.326 (9.5); 7.318 (1.1); 7.286 (5.3); 7.273 (5.2); 7.140 (1.6); 7.138 (2.9); 7.135 (1.7); 7.119 (4.8); 7.103 (1.3); 7.101 (2.4); 7.098 (1.3); 6.944 (1.5); 6.940 (6.5); 6.938 (8.1); 6.932 (2.2); 6.923 (2.3); 6.921 (3.9); 6.919 (7.0); 6.916 (6.1); 6.910 (0.7); 6.889 (1.2); 6.881 (9.9); 6.876 (2.9); 6.864 (2.9); 6.859 (9.2); 6.852 (0.9); 5.949 (0.5); 5.839 (12.0); 4.726 (1.8); 4.690 (5.6); 4.668 (5.6); 4.632 (1.8); 3.431 (3.2); 3.395 (4.1); 3.345 (20.4); 3.204 (4.1); 3.168 (3.2); 2.545 (45.2); 2.523 (0.4); 2.514 (5.0); 2.510 (10.2); 2.505 (13.4); 2.501 (9.5); 2.496 (4.4); 0.000 (1.1) |
Example I-02: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.532 (6.7); 8.422 (12.3); 8.315 (0.7); 8.273 (14.3); 8.266 (7.6); 8.254 (7.7); 8.152 (4.5); 8.131 (5.6); 8.035 (6.6); 7.925 (5.6); 7.907 (16.0); 7.808 (2.7); 7.804 (3.8); 7.787 (3.9); 7.665 (5.3); 7.662 (7.0); 7.644 (7.9); 7.581 (7.9); 7.559 (11.2); 7.549 (2.3); 7.532 (4.5); 7.528 (2.3); 7.512 (2.9); 7.486 (0.4); 7.475 (2.0); 7.461 (4.9); 7.456 (4.4); 7.446 (13.1); 7.442 (12.2); 7.425 (10.8); 7.378 (0.3); 7.363 (3.4); 7.349 (1.6); 7.344 (4.4); 7.340 (1.4); 7.326 (1.6); 7.293 (5.7); 7.281 (5.7); 6.030 (11.3); 5.881 (12.4); 4.714 (0.7); 4.678 (8.4); 4.673 (8.4); 4.637 (0.7); 3.495 (3.4); 3.459 (4.4); 3.355 (0.9); 3.325 (468.6); 3.304 (0.8); 3.287 (0.4); 3.280 (0.4); 3.262 (0.4); 3.245 (4.4); 3.209 (3.5); 2.995 (0.7); 2.675 (1.4); 2.671 (2.0); 2.666 (1.4); 2.541 (99.0); 2.524 (5.4); 2.511 (119.5); 2.506 (240.7); 2.502 (314.6); 2.497 (222.8); 2.493 (104.1); 2.459 (0.6); 2.444 (0.5); 2.439 (0.4); 2.367 (0.5); 2.333 (1.5); 2.328 (2.0); 2.324 (1.4); 1.235 (0.6); 0.008 (0.5); 0.000 (12.8); - 0.008 (0.4) |
Example I-03: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.319 (8.0); 8.315 (8.1); 8.258 (15.8); 8.201 (5.1); 8.190 (5.2); 8.189 (5.2); 7.900 (16.0); 7.408 (0.9); 7.402 (5.7); 7.397 (2.2); 7.384 (8.5); 7.381 (8.4); 7.376 (1.4); 7.367 (2.6); 7.362 (7.2); 7.357 (1.1); 7.339 (10.0); 7.335 (3.6); 7.318 (11.1); 7.310 (1.4); 7.203 (3.2); 7.190 (3.9); 7.188 (4.0); 7.175 (3.1); 7.137 (3.3); 7.135 (2.2); 7.119 (5.6); 7.100 (2.7); 7.098 (1.6); 6.926 (7.6); 6.924 (9.5); 6.919 (2.8); 6.904 (8.3); 6.902 (7.4); 6.896 (1.0); 6.878 (1.4); 6.871 (12.0); 6.867 (3.9); 6.849 (11.1); 6.842 (1.2); 5.947 (0.4); 5.810 (14.1); 4.672 (16.0); 3.342 (34.2); 3.303 (4.7); 3.092 (4.6); 3.058 (3.6); 3.000 (0.4); 2.713 (0.5); 2.544 (105.7); 2.526 (0.5); 2.522 (0.6); 2.513 (7.8); 2.509 (15.9); 2.504 (21.1); 2.500 (15.3); 2.495 (7.4); 2.370 (0.5); 0.000 (7.2) |
Example I-04: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.303 (7.7); 8.299 (7.7); 8.257 (15.4); 8.179 (4.9); 8.167 (5.0); 7.889 (16.0); 7.665 (6.0); 7.662 (7.9); 7.657 (2.3); 7.644 (8.9); 7.570 (8.9); 7.549 (12.2); 7.460 (4.7); 7.456 (1.9); 7.442 (10.2); 7.439 (6.7); 7.432 (11.8); 7.427 (5.4); 7.422 (6.8); 7.411 (8.4); 7.365 (2.2); 7.362 (3.6); 7.359 (2.2); 7.348 (1.7); 7.343 (4.9); 7.339 (1.3); 7.328 (1.1); 7.325 (1.7); 7.322 (1.0); 7.220 (3.0); 7.207 (3.8); 7.205 (3.8); 7.192 (2.9); 5.853 (14.2); 4.681 (15.0); 3.396 (3.6); 3.361 (4.7); 3.333 (227.1); 3.131 (4.3); 3.096 (3.4); 2.996 (0.7); 2.711 (0.6); 2.676 (0.4); 2.671 (0.5); 2.667 (0.4); 2.567 (0.4); 2.562 (0.4); 2.558 (0.6); 2.542 (152.4); 2.525 (1.4); 2.511 (30.9); 2.507 (62.0); 2.502 (80.7); 2.498 (56.9); 2.493 (26.6); 2.368 (0.6); 2.333 (0.4); 2.329 (0.5); 2.324 (0.4); 0.008 (0.6); 0.000 (17.2); -0.009 (0.5) |
Example I-05: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.192 (15.6); 8.151 (6.9); 8.138 (7.0); 7.870 (16.0); 7.387 (0.6); 7.379 (5.1); 7.374 (2.2); 7.365 (5.8); 7.357 (6.1); 7.348 (2.5); 7.343 (5.5); 7.335 (0.6); 7.139 (8.5); 7.097 (0.7); 7.089 (6.0); 7.084 (1.9); 7.067 (10.9); 7.050 (1.8); 7.045 (5.1); 7.037 (0.5); 7.019 (4.7); 7.016 (4.5); 7.006 (4.6); 7.003 (4.4); 5.883 (15.3); 4.631 (3.4); 4.596 (7.1); 4.546 (7.0); 4.510 (3.4); 3.351 (29.4); 3.276 (3.8); 3.242 (5.8); 3.144 (5.6); 3.110 (3.6); 3.005 (0.4); 2.719 (0.4); 2.568 (0.4); 2.550 (93.6); 2.533 (0.5); 2.528 (0.4); 2.519 (6.0); 2.515 (12.4); 2.510 (16.6); 2.505 (11.8); 2.501 (5.5); 2.375 (0.4); 2.081 (0.4) |
Example I-06: 1H-NMR (400.0 MHz, CD3CN): |
δ= 8.427 (11.6); 8.247 (7.2); 8.234 (7.3); 8.067 (12.1); 7.926 (1.6); 7.814 (11.5); 7.755 (0.4); 7.733 (0.4); 7.379 (1.1); 7.371 (11.1); 7.365 (3.6); 7.354 (4.0); 7.348 (12.2); 7.343 (2.0); 7.335 (11.2); 7.330 (3.6); 7.318 (4.1); 7.313 (12.1); 7.306 (1.3); 7.150 (6.3); 7.138 (6.2); 7.038 (0.4); 7.016 (0.4); 6.942 (1.4); 6.933 (12.3); 6.928 (3.8); 6.916 (3.8); 6.911 (11.2); 6.900 (12.1); 6.895 (3.7); 6.883 (3.7); 6.878 (10.5); 6.870 (1.1); 4.731 (4.8); 4.695 (8.3); 4.606 (8.4); 4.570 (4.9); 4.488 (10.3); 4.085 (0.6); 4.068 (1.7); 4.050 (1.7); 4.032 (0.6); 3.874 (1.8); 3.383 (3.8); 3.348 (7.9); 3.289 (8.3); 3.254 (4.0); 2.889 (16.0); 2.772 (14.0); 2.157 (27.3); 2.107 (0.3); 1.972 (7.8); 1.964 (1.7); 1.958 (4.0); 1.952 (19.9); 1.946 (35.5); 1.940 (47.2); 1.934 (32.3); 1.928 (16.4); 1.436 (0.9); 1.221 (2.0); 1.203 (3.9); 1.186 (1.9); 0.146 (0.7); 0.008 (6.2); 0.000 (135.8); -0.008 (5.6); -0.150 (0.7) |
Example I-07: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.771 (0.5); 8.366 (0.8); 8.316 (1.8); 8.298 (16.0); 8.005 (8.6); 7.992 (8.9); 7.775 (15.7); 7.576 (0.3); 7.525 (0.5); 7.513 (0.6); 7.491 (0.4); 7.475 (0.5); 7.441 (5.4); 7.423 (6.1); 7.421 (6.1); 7.404 (0.5); 7.394 (0.6); 7.383 (0.5); 7.372 (0.7); 7.350 (0.5); 7.334 (0.4); 7.304 (4.8); 7.288 (5.0); 7.284 (5.5); 7.257 (2.6); 7.253 (2.7); 7.238 (4.9); 7.234 (4.5); 7.219 (3.0); 7.215 (2.6); 7.130 (3.8); 7.110 (6.2); 7.095 (9.5); 7.082 (3.9); 6.143 (14.6); 5.137 (5.7); 5.101 (6.9); 4.831 (6.8); 4.795 (5.5); 4.648 (0.8); 3.833 (4.8); 3.798 (5.3); 3.480 (0.4); 3.445 (0.6); 3.439 (0.6); 3.333 (1808.3); 3.258 (5.7); 3.224 (4.9); 2.995 (0.9); 2.711 (1.7); 2.675 (3.3); 2.671 (4.5); 2.611 (0.3); 2.542 (382.5); 2.506 (543.5); 2.502 (706.6); 2.498 (533.1); 2.409 (0.5); 2.367 (1.9); 2.329 (4.5); 2.324 (3.5); 1.298 (0.4); 1.258 (0.6); 1.235 (2.5); 0.146 (0.5); 0.007 (4.6); 0.000 (112.9); - 0.150 (0.6) |
Example I-08: 1H-NMR (499.9 MHz, CDCl3): |
δ= 8.027 (10.0); 8.017 (10.3); 7.947 (15.0); 7.836 (16.0); 7.268 (2.3); 7.264 (1.7); 7.255 (2.6); 7.250 (4.4); 7.237 (4.3); 7.232 (2.9); 7.219 (2.3); 7.085 (4.7); 7.075 (9.0); 7.065 (4.7); 6.815 (2.3); 6.810 (2.6); 6.799 (2.5); 6.793 (3.2); 6.791 (3.2); 6.786 (2.8); 6.774 (2.4); 6.769 (2.6); 6.711 (2.2); 6.706 (2.2); 6.694 (3.8); 6.692 (3.6); 6.690 (3.7); 6.677 (2.1); 6.673 (2.0); 5.162 (0.7); 4.975 (6.5); 4.947 (7.2); 4.484 (7.6); 4.456 (6.8); 3.313 (3.4); 3.286 (8.3); 3.252 (9.3); 3.225 (3.7); 2.041 (0.6); 1.257 (0.6); 0.006 (0.4); 0.000 (8.8) |
Example I-09: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.308 (16.0); 8.047 (8.1); 8.035 (8.4); 7.764 (15.4); 7.654 (0.5); 7.633 (0.6); 7.597 (8.2); 7.592 (8.4); 7.536 (0.5); 7.532 (0.5); 7.461 (0.5); 7.456 (0.5); 7.349 (0.4); 7.341 (0.6); 7.336 (0.4); 7.320 (0.4); 7.313 (0.8); 7.292 (0.4); 7.260 (5.3); 7.238 (12.0); 7.225 (1.0); 7.206 (6.5); 7.201 (6.3); 7.185 (2.9); 7.180 (3.0); 7.143 (3.9); 7.130 (7.2); 7.118 (3.7); 7.101 (1.3); 6.262 (14.2); 5.751 (1.0); 5.189 (5.7); 5.153 (6.4); 4.757 (6.4); 4.721 (5.5); 3.811 (4.9); 3.777 (5.3); 3.339 (182.3); 3.310 (0.7); 3.294 (5.6); 3.259 (4.8); 2.997 (0.3); 2.713 (0.5); 2.673 (0.4); 2.543 (106.8); 2.508 (50.6); 2.504 (66.0); 2.370 (0.5); 2.331 (0.4); 1.234 (0.7); 0.000 (12.4) |
Example I-10: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.257 (15.9); 8.036 (8.3); 8.024 (8.5); 7.866 (15.6); 7.392 (0.3); 7.366 (8.1); 7.344 (15.5); 7.303 (16.0); 7.281 (8.2); 7.164 (3.9); 7.152 (7.2); 7.139 (3.8); 5.966 (14.4); 4.730 (1.8); 4.694 (9.8); 4.682 (9.5); 4.646 (1.8); 3.410 (4.7); 3.368 (56.6); 3.178 (5.5); 3.144 (4.2); 2.719 (0.6); 2.549 (97.0); 2.509 (14.0); 2.506 (10.9); 2.375 (0.6); 0.000 (2.4) |
Example I-11: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.420 (12.7); 8.279 (7.8); 8.266 (10.1); 8.262 (14.8); 7.878 (13.8); 7.353 (7.5); 7.348 (3.0); 7.336 (4.4); 7.331 (14.1); 7.326 (2.3); 7.283 (14.5); 7.278 (4.1); 7.266 (9.4); 7.262 (8.6); 7.254 (6.8); 5.927 (12.6); 4.671 (16.0); 3.463 (4.2); 3.427 (5.3); 3.328 (49.1); 3.208 (5.3); 3.172 (4.1); 2.542 (49.4); 2.512 (21.4); 2.507 (40.1); 2.503 (50.5); 2.498 (36.0); 2.494 (17.3); 2.330 (0.3); 0.000 (2.5) |
Example I-12: 1H-NMR (400.0 MHz, CD3CN): |
δ= 12.244 (2.1); 8.457 (7.6); 8.228 (6.5); 8.216 (7.1); 8.120 (12.2); 8.090 (16.0); 7.829 (0.5); 7.807 (0.5); 7.718 (7.0); 7.697 (0.4); 7.438 (2.6); 7.434 (2.8); 7.418 (3.1); 7.414 (3.3); 7.409 (2.8); 7.406 (2.7); 7.389 (3.1); 7.386 (3.2); 7.250 (1.3); 7.246 (1.4); 7.231 (2.6); 7.227 (2.5); 7.212 (1.6); 7.208 (1.5); 7.151 (2.0); 7.148 (2.1); 7.140 (4.3); 7.128 (6.1); 7.113 (1.3); 7.110 (1.2); 5.466 (4.3); 5.430 (4.7); 4.858 (4.7); 4.593 (4.7); 4.557 (4.3); 3.729 (2.8); 3.694 (4.8); 3.600 (5.4); 3.564 (3.1); 3.430 (0.5); 3.413 (0.5); 2.894 (0.8); 2.778 (0.7); 2.590 (1.2); 2.560 (0.4); 2.492 (1.2); 2.487 (1.4); 2.482 (1.2); 2.245 (6.8); 2.122 (1.9); 2.115 (2.1); 2.109 (2.1); 2.103 (1.8); 2.097 (1.5); 2.088 (1.3); 1.966 (8.0); 1.960 (13.4); 1.954 (53.7); 1.948 (93.7); 1.942 (121.8); 1.936 (84.4); 1.930 (43.5); 1.782 (0.4); 1.776 (0.7); 1.770 (0.8); 1.764 (0.6); 1.758 (0.4); 1.270 (1.4); 1.141 (0.6); 1.124 (1.1); 1.106 (0.6); 0.882 (0.4); 0.858 (0.4); 0.007 (2.0); 0.000 (42.5); -0.008 (1.8) |
Example I-13: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.297 (8.0); 8.293 (8.1); 8.242 (15.9); 8.185 (5.0); 8.183 (5.0); 8.173 (5.1); 8.171 (5.2); 7.866 (16.0); 7.373 (0.6); 7.365 (5.0); 7.360 (2.2); 7.352 (5.7); 7.343 (6.0); 7.335 (2.5); 7.329 (5.4); 7.322 (0.7); 7.178 (3.2); 7.166 (3.9); 7.163 (4.0); 7.150 (3.1); 7.059 (0.7); 7.052 (6.1); 7.047 (2.0); 7.029 (11.1); 7.012 (1.9); 7.007 (5.3); 6.999 (0.5); 5.861 (15.0); 4.713 (1.0); 4.677 (10.2); 4.672 (9.8); 4.636 (0.9); 3.360 (4.8); 3.350 (37.4); 3.326 (4.9); 3.095 (4.7); 3.060 (3.7); 2.715 (0.4); 2.546 (90.8); 2.529 (0.4); 2.524 (0.4); 2.515 (5.2); 2.511 (10.9); 2.506 (14.5); 2.501 (10.4); 2.497 (5.0); 2.371 (0.4); 0.000 (4.7) |
Example I-14: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.804 (0.5); 8.316 (0.4); 8.169 (5.9); 8.133 (16.0); 7.367 (3.7); 7.350 (5.7); 7.325 (0.4); 7.289 (2.3); 7.272 (5.1); 7.253 (3.3); 7.234 (2.4); 7.216 (2.4); 7.199 (0.7); 6.916 (4.3); 5.965 (6.8); 4.605 (2.1); 4.569 (3.6); 4.487 (3.6); 4.451 (2.1); 3.444 (2.5); 3.409 (3.2); 3.383 (0.4); 3.331 (301.1); 3.182 (3.2); 3.147 (2.5); 2.671 (1.2); 2.542 (69.3); 2.506 (151.6); 2.502 (190.0); 2.498 (140.1); 2.435 (0.3); 2.368 (0.4); 2.329 (1.2); 1.236 (0.8); 0.000 (40.0) |
Example I-15: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 9.235 (1.0); 8.576 (1.4); 8.315 (0.8); 8.277 (4.6); 8.172 (1.2); 8.141 (14.4); 7.905 (5.3); 7.392 (5.8); 7.378 (6.6); 7.370 (7.2); 7.361 (3.2); 7.356 (6.4); 7.261 (0.5); 7.240 (0.9); 7.226 (0.7); 7.218 (0.3); 7.197 (1.0); 7.190 (1.4); 7.175 (1.0); 7.153 (0.4); 7.080 (6.8); 7.058 (12.6); 7.036 (6.4); 7.028 (9.5); 7.025 (9.1); 6.872 (0.7); 5.961 (16.0); 5.577 (0.6); 4.739 (2.2); 4.703 (6.0); 4.669 (6.1); 4.634 (2.2); 4.368 (0.6); 4.364 (0.6); 4.355 (0.6); 4.100 (0.4); 4.087 (0.4); 3.902 (8.8); 3.485 (4.9); 3.449 (6.1); 3.328 (327.4); 3.267 (0.7); 3.242 (0.4); 3.221 (6.3); 3.185 (5.0); 3.176 (2.5); 3.163 (2.1); 2.995 (0.8); 2.676 (1.6); 2.672 (2.2); 2.667 (1.6); 2.542 (14.5); 2.525 (6.0); 2.511 (138.9); 2.507 (288.6); 2.503 (402.7); 2.498 (306.0); 2.433 (0.4); 2.334 (1.7); 2.329 (2.4); 2.325 (1.7); 2.295 (0.4); 1.909 (0.4); 1.235 (0.3); 0.146 (0.4); 0.008 (2.7); 0.000 (85.2); -0.008 (3.4); -0.150 (0.4) |
Example I-16: 1H-NMR (400.0 MHz, CD3CN): |
δ= 8.183 (4.8); 8.178 (4.9); 8.171 (5.0); 8.167 (4.8); 8.075 (14.6); 7.775 (14.5); 7.592 (5.2); 7.587 (6.2); 7.583 (5.9); 7.573 (6.2); 7.568 (8.2); 7.561 (16.0); 7.539 (15.3); 7.518 (5.3); 7.163 (5.5); 7.151 (5.4); 7.144 (5.1); 7.132 (4.9); 4.820 (7.8); 4.784 (10.8); 4.681 (12.4); 4.613 (10.5); 4.577 (7.5); 3.412 (4.4); 3.375 (11.6); 3.334 (11.7); 3.298 (4.5); 2.889 (2.9); 2.772 (2.5); 2.473 (0.7); 2.469 (1.5); 2.464 (2.1); 2.459 (1.4); 2.454 (0.7); 2.160 (614.5); 2.127 (1.6); 2.120 (2.0); 2.114 (2.8); 2.108 (3.5); 2.101 (2.5); 2.095 (1.4); 1.964 (31.6); 1.958 (52.4); 1.953 (234.4); 1.946 (413.7); 1.940 (542.3); 1.934 (373.5); 1.928 (193.3); 1.781 (1.3); 1.775 (2.3); 1.769 (3.2); 1.762 (2.2); 1.756 (1.1); 1.286 (0.4); 1.204 (0.6); 0.000 (1.7) |
Example I-17: 1H-NMR (400.0 MHz, CD3CN): |
δ= 8.289 (0.4); 8.182 (2.9); 8.177 (3.1); 8.170 (3.1); 8.165 (3.2); 8.072 (9.6); 8.058 (0.3); 7.925 (1.7); 7.788 (9.2); 7.591 (2.9); 7.586 (3.0); 7.571 (3.2); 7.567 (3.3); 7.356 (4.9); 7.353 (6.0); 7.290 (0.8); 7.286 (0.6); 7.280 (1.3); 7.276 (2.2); 7.271 (1.9); 7.266 (4.4); 7.263 (4.4); 7.257 (1.4); 7.252 (1.6); 7.246 (7.0); 7.243 (5.2); 7.238 (4.0); 7.233 (4.9); 7.230 (4.8); 7.220 (0.6); 7.166 (3.4); 7.154 (3.3); 7.147 (3.3); 7.135 (3.1); 4.770 (4.9); 4.735 (7.1); 4.604 (7.6); 4.578 (7.2); 4.542 (5.0); 3.381 (3.3); 3.345 (7.4); 3.290 (7.5); 3.254 (3.4); 2.889 (16.0); 2.771 (14.3); 2.469 (0.4); 2.464 (0.6); 2.460 (0.5); 2.161 (134.4); 2.120 (0.5); 2.114 (0.7); 2.107 (0.9); 2.101 (0.6); 2.095 (0.4); 1.964 (8.4); 1.958 (12.8); 1.952 (59.7); 1.946 (106.3); 1.940 (139.7); 1.934 (95.9); 1.928 (49.6); 1.781 (0.4); 1.775 (0.6); 1.768 (0.8); 1.762 (0.6); 1.756 (0.4); 1.712 (0.4); 1.483 (0.3); 1.434 (0.7); 0.983 (2.3); 0.146 (0.4); 0.008 (3.0); 0.000 (92.3); -0.009 (3.2); -0.150 (0.4) |
Example I-18: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.410 (9.7); 8.272 (6.3); 8.259 (16.0); 7.885 (10.8); 7.377 (0.5); 7.369 (3.6); 7.364 (1.6); 7.356 (4.1); 7.347 (4.4); 7.339 (1.8); 7.333 (4.0); 7.326 (0.5); 7.255 (4.7); 7.242 (4.6); 7.067 (0.5); 7.059 (4.2); 7.054 (1.3); 7.037 (7.8); 7.020 (1.3); 7.015 (3.7); 7.007 (0.4); 5.882 (9.8); 4.711 (0.6); 4.676 (7.4); 4.671 (7.3); 4.635 (0.6); 3.449 (3.1); 3.414 (3.9); 3.333 (25.9); 3.201 (3.9); 3.165 (3.1); 2.543 (34.5); 2.526 (0.4); 2.513 (8.2); 2.508 (16.4); 2.504 (21.5); 2.499 (15.4); 2.495 (7.3); 0.000 (1.1) |
Example I-19: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.508 (0.7); 8.425 (11.2); 8.277 (7.0); 8.266 (16.0); 8.092 (0.5); 8.070 (0.5); 8.020 (0.6); 7.913 (12.7); 7.486 (1.5); 7.478 (1.5); 7.463 (1.7); 7.457 (2.5); 7.451 (1.5); 7.436 (1.4); 7.428 (1.4); 7.340 (1.1); 7.333 (8.1); 7.328 (2.7); 7.316 (3.1); 7.311 (8.9); 7.303 (1.0); 7.264 (5.2); 7.251 (5.0); 7.221 (1.2); 7.207 (1.2); 7.199 (2.7); 7.185 (2.7); 7.176 (2.1); 7.162 (2.0); 7.151 (1.6); 7.148 (1.5); 7.143 (1.4); 7.140 (1.3); 7.130 (1.7); 7.127 (2.2); 7.124 (2.2); 7.120 (1.9); 7.108 (0.9); 7.104 (1.1); 7.101 (0.9); 7.097 (0.7); 6.847 (1.2); 6.840 (8.7); 6.818 (8.0); 6.810 (0.8); 5.956 (1.0); 5.837 (10.6); 4.703 (1.7); 4.668 (5.4); 4.646 (5.4); 4.610 (1.7); 3.421 (3.1); 3.386 (3.9); 3.350 (17.0); 3.196 (3.9); 3.161 (3.0); 2.547 (48.4); 2.517 (4.4); 2.512 (8.9); 2.508 (11.7); 2.503 (8.3); 2.499 (3.9); 0.000 (0.6) |
Example I-20: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.507 (2.3); 8.308 (7.6); 8.304 (7.8); 8.241 (15.5); 8.187 (4.9); 8.186 (4.9); 8.175 (5.0); 8.173 (4.9); 8.090 (1.8); 8.085 (0.6); 8.073 (0.6); 8.068 (1.9); 8.020 (2.2); 7.891 (16.0); 7.559 (0.4); 7.500 (0.4); 7.487 (1.9); 7.480 (1.9); 7.465 (2.2); 7.459 (3.2); 7.453 (2.1); 7.438 (1.8); 7.431 (1.6); 7.321 (9.6); 7.316 (3.5); 7.304 (3.6); 7.299 (10.5); 7.292 (1.3); 7.224 (0.4); 7.222 (0.4); 7.217 (0.4); 7.214 (0.4); 7.209 (1.2); 7.201 (0.4); 7.195 (1.6); 7.186 (4.6); 7.172 (6.7); 7.165 (4.1); 7.156 (3.8); 7.152 (4.1); 7.150 (4.9); 7.146 (2.5); 7.143 (2.1); 7.133 (2.5); 7.130 (2.9); 7.125 (3.7); 7.107 (1.4); 7.103 (2.3); 6.835 (1.3); 6.828 (10.7); 6.805 (9.9); 6.798 (1.0); 5.954 (3.5); 5.811 (14.1); 4.651 (14.5); 3.357 (91.9); 3.326 (3.6); 3.291 (4.3); 3.084 (4.3); 3.049 (3.3); 3.002 (0.6); 2.716 (0.6); 2.546 (126.6); 2.530 (0.5); 2.516 (7.6); 2.512 (15.6); 2.507 (20.7); 2.502 (14.9); 2.498 (7.1); 2.373 (0.6); 2.372 (0.6); 0.000 (4.7) |
Example I-21: 1H-NMR (400.0 MHz, CD3CN): |
δ= 12.004 (0.3); 11.991 (0.3); 8.420 (16.0); 8.330 (0.4); 8.266 (0.5); 8.244 (10.3); 8.231 (10.4); 8.186 (0.5); 8.113 (0.4); 8.067 (15.9); 8.016 (0.5); 8.004 (0.5); 7.977 (0.4); 7.929 (1.2); 7.800 (15.0); 7.368 (8.1); 7.366 (9.0); 7.362 (4.2); 7.298 (1.6); 7.294 (1.4); 7.288 (2.6); 7.285 (4.0); 7.279 (3.3); 7.275 (5.7); 7.270 (6.9); 7.265 (2.1); 7.260 (1.9); 7.251 (10.6); 7.250 (10.5); 7.248 (8.7); 7.243 (6.8); 7.238 (8.9); 7.235 (8.2); 7.229 (0.9); 7.225 (0.8); 7.165 (8.7); 7.152 (8.4); 5.448 (9.4); 4.746 (7.7); 4.710 (11.9); 4.613 (15.8); 4.590 (12.0); 4.554 (7.7); 3.409 (6.1); 3.373 (11.2); 3.295 (11.7); 3.260 (6.3); 2.890 (10.7); 2.774 (9.2); 2.171 (2.9); 1.965 (2.7); 1.959 (4.4); 1.953 (20.4); 1.947 (36.0); 1.940 (47.1); 1.934 (32.2); 1.928 (16.5); 0.008 (1.0); 0.000 (29.2); -0.009 (0.9) |
Example I-22: 1H-NMR (400.0 MHz, CD3CN): |
δ= 8.425 (8.3); 8.238 (5.5); 8.226 (5.6); 8.051 (8.5); 7.806 (8.3); 7.357 (0.7); 7.352 (3.7); 7.346 (1.8); 7.339 (1.0); 7.333 (5.8); 7.330 (5.7); 7.317 (2.2); 7.311 (6.7); 7.298 (0.5); 7.292 (4.3); 7.290 (4.3); 7.272 (2.5); 7.271 (2.8); 7.188 (2.5); 7.185 (3.5); 7.184 (3.4); 7.182 (2.9); 7.169 (1.9); 7.166 (2.3); 7.164 (2.5); 7.162 (2.1); 7.143 (4.6); 7.129 (4.7); 7.124 (3.0); 7.122 (1.8); 7.109 (1.7); 7.106 (3.9); 7.090 (1.1); 7.087 (1.8); 7.085 (1.2); 6.889 (2.3); 6.885 (5.6); 6.883 (5.4); 6.881 (7.8); 6.878 (6.9); 6.861 (2.5); 6.859 (2.6); 6.855 (1.9); 6.853 (1.7); 6.801 (5.2); 6.798 (6.6); 6.793 (2.2); 6.781 (3.3); 6.779 (5.7); 6.776 (5.3); 6.770 (0.8); 4.739 (3.8); 4.703 (6.1); 4.594 (6.0); 4.558 (5.6); 4.551 (5.6); 4.085 (2.1); 4.068 (6.3); 4.050 (6.4); 4.032 (2.1); 3.396 (3.1); 3.361 (5.4); 3.275 (5.8); 3.240 (3.3); 2.888 (1.7); 2.772 (1.5); 2.770 (1.5); 2.181 (30.8); 1.972 (28.5); 1.965 (1.9); 1.958 (2.8); 1.952 (13.4); 1.946 (23.6); 1.940 (31.3); 1.934 (21.5); 1.928 (11.1); 1.436 (2.1); 1.221 (8.2); 1.203 (16.0); 1.185 (8.0); 0.146 (0.4); 0.017 (0.4); 0.016 (0.4); 0.008 (4.3); 0.000 (95.6); -0.009 (4.6); -0.150 (0.4) |
Example I-23: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.252 (12.7); 8.029 (6.5); 8.017 (6.6); 7.874 (12.5); 7.383 (4.3); 7.369 (5.1); 7.361 (5.5); 7.347 (4.8); 7.157 (3.2); 7.144 (5.9); 7.132 (3.0); 7.079 (4.8); 7.057 (8.8); 7.035 (4.2); 5.922 (10.7); 4.691 (16.0); 3.399 (3.9); 3.369 (39.9); 3.163 (4.5); 3.129 (3.4); 2.719 (0.5); 2.550 (88.1); 2.514 (8.5); 2.510 (11.1); 2.375 (0.5); 0.000 (2.4) |
Example I-24: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.516 (6.0); 8.221 (13.3); 8.195 (0.3); 8.180 (6.7); 8.176 (2.2); 8.170 (2.4); 8.166 (6.8); 8.108 (0.6); 8.101 (5.1); 8.096 (1.5); 8.084 (1.7); 8.079 (5.4); 8.071 (0.6); 8.027 (6.3); 7.910 (14.7); 7.519 (0.4); 7.514 (2.3); 7.509 (0.9); 7.495 (3.7); 7.493 (3.5); 7.487 (0.6); 7.479 (1.2); 7.474 (3.2); 7.468 (0.5); 7.409 (1.1); 7.403 (5.4); 7.398 (2.1); 7.391 (1.5); 7.385 (8.0); 7.382 (7.7); 7.376 (1.2); 7.368 (2.7); 7.363 (7.3); 7.354 (9.6); 7.349 (3.2); 7.337 (3.5); 7.332 (10.6); 7.325 (1.2); 7.305 (0.9); 7.302 (1.5); 7.300 (0.9); 7.284 (2.4); 7.268 (0.7); 7.265 (1.1); 7.262 (0.6); 7.199 (0.4); 7.178 (3.4); 7.176 (4.1); 7.170 (1.1); 7.159 (2.2); 7.157 (3.6); 7.154 (3.1); 7.145 (2.1); 7.143 (3.3); 7.141 (2.1); 7.136 (1.1); 7.128 (7.4); 7.125 (6.6); 7.111 (2.1); 7.106 (7.6); 7.099 (0.7); 7.076 (3.6); 7.073 (5.7); 7.066 (7.8); 7.063 (16.0); 7.051 (0.5); 7.039 (0.4); 6.951 (0.7); 6.942 (7.3); 6.939 (8.9); 6.934 (2.5); 6.923 (5.7); 6.920 (9.4); 6.917 (13.6); 6.911 (4.1); 6.899 (3.4); 6.894 (10.2); 6.887 (1.0); 5.954 (10.4); 5.831 (13.8); 4.637 (1.9); 4.602 (6.6); 4.583 (6.5); 4.547 (1.8); 3.348 (24.3); 3.261 (3.2); 3.228 (4.7); 3.121 (4.7); 3.087 (3.2); 3.006 (1.5); 3.002 (0.3); 2.719 (0.6); 2.570 (0.4); 2.550 (126.2); 2.532 (0.6); 2.519 (9.3); 2.514 (18.9); 2.510 (24.7); 2.505 (17.4); 2.501 (8.1); 2.375 (0.5); 2.082 (0.7); 1.467 (0.4) |
Example I-25: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.507 (9.8); 8.435 (1.5); 8.193 (9.6); 8.172 (2.8); 8.160 (7.0); 8.147 (4.5); 8.100 (14.6); 8.092 (8.3); 8.087 (2.6); 8.075 (3.1); 8.070 (8.6); 8.063 (0.9); 8.053 (0.6); 8.022 (10.2); 7.895 (10.4); 7.597 (1.3); 7.590 (1.4); 7.575 (1.5); 7.569 (2.1); 7.562 (1.5); 7.547 (1.4); 7.540 (1.4); 7.506 (2.0); 7.495 (1.8); 7.493 (1.8); 7.483 (3.7); 7.474 (3.0); 7.469 (4.1); 7.460 (1.8); 7.452 (1.7); 7.446 (2.8); 7.328 (7.1); 7.322 (5.4); 7.316 (2.0); 7.311 (2.8); 7.306 (8.4); 7.299 (5.3); 7.255 (1.0); 7.251 (1.1); 7.248 (1.0); 7.244 (1.0); 7.234 (1.9); 7.231 (1.8); 7.228 (1.8); 7.223 (1.6); 7.220 (1.8); 7.212 (2.3); 7.208 (1.4); 7.204 (1.9); 7.196 (3.1); 7.189 (1.3); 7.181 (2.4); 7.174 (2.6); 7.159 (1.9); 7.154 (2.3); 7.151 (2.1); 7.147 (2.1); 7.144 (2.2); 7.134 (3.1); 7.129 (9.7); 7.124 (4.9); 7.111 (3.3); 7.107 (7.8); 7.090 (5.7); 7.063 (3.6); 7.044 (3.2); 7.041 (3.0); 7.032 (3.1); 7.029 (2.9); 7.017 (2.0); 7.014 (1.9); 7.004 (1.9); 7.001 (1.8); 6.878 (4.5); 6.863 (7.9); 6.856 (5.4); 6.841 (6.7); 6.833 (0.7); 5.955 (16.0); 5.878 (5.8); 5.823 (9.5); 5.805 (1.0); 4.607 (1.5); 4.572 (4.4); 4.554 (2.1); 4.546 (4.5); 4.519 (2.2); 4.511 (1.7); 4.364 (2.1); 4.328 (1.5); 3.339 (99.6); 3.243 (2.5); 3.237 (1.8); 3.209 (3.7); 3.113 (3.3); 3.079 (2.2); 3.062 (1.9); 3.029 (1.4); 3.004 (2.1); 2.719 (0.8); 2.684 (0.4); 2.679 (0.5); 2.674 (0.4); 2.571 (0.4); 2.568 (0.7); 2.549 (216.2); 2.538 (1.1); 2.532 (1.5); 2.519 (30.5); 2.514 (60.8); 2.510 (79.1); 2.505 (55.8); 2.501 (25.9); 2.375 (0.8); 2.341 (0.4); 2.337 (0.5); 2.332 (0.4); 2.083 (0.7); 1.242 (0.3) |
Example I-26: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.813 (0.5); 8.725 (0.3); 8.651 (0.8); 8.535 (9.3); 8.353 (3.6); 8.349 (3.5); 8.295 (0.7); 8.272 (10.2); 8.198 (6.7); 8.153 (6.7); 8.132 (8.0); 8.100 (1.0); 8.085 (0.4); 8.063 (0.4); 8.038 (9.2); 7.963 (0.5); 7.941 (0.7); 7.926 (8.2); 7.903 (14.9); 7.874 (0.4); 7.852 (0.7); 7.843 (0.4); 7.828 (0.7); 7.822 (0.6); 7.809 (4.6); 7.805 (5.9); 7.787 (6.3); 7.762 (1.0); 7.751 (0.8); 7.744 (0.9); 7.707 (5.9); 7.701 (4.9); 7.686 (7.6); 7.682 (5.7); 7.669 (5.3); 7.666 (6.4); 7.648 (7.3); 7.629 (1.0); 7.607 (1.2); 7.593 (6.6); 7.572 (8.6); 7.551 (3.1); 7.533 (6.9); 7.513 (4.9); 7.494 (2.9); 7.476 (7.9); 7.468 (5.3); 7.457 (8.1); 7.447 (13.7); 7.429 (7.8); 7.426 (7.7); 7.400 (2.2); 7.381 (2.8); 7.369 (3.2); 7.350 (3.9); 7.332 (1.6); 7.295 (5.0); 7.275 (4.6); 7.254 (4.4); 7.242 (4.3); 7.077 (0.7); 7.057 (0.6); 6.963 (0.4); 6.950 (0.4); 6.823 (2.6); 6.810 (2.6); 6.723 (2.8); 6.031 (16.0); 5.915 (9.4); 5.589 (1.3); 5.575 (2.9); 5.562 (1.3); 5.513 (0.3); 4.729 (0.6); 4.693 (7.0); 4.689 (6.9); 4.653 (0.6); 4.369 (2.8); 4.364 (3.0); 4.355 (2.9); 4.351 (2.7); 3.433 (0.5); 3.422 (0.4); 3.393 (3.3); 3.342 (830.2); 3.299 (1.7); 3.290 (1.5); 3.280 (1.1); 3.268 (0.9); 3.257 (0.6); 3.247 (0.5); 3.239 (0.5); 3.229 (0.5); 3.219 (0.3); 3.194 (0.3); 3.127 (3.3); 3.092 (2.6); 3.003 (0.5); 2.996 (2.2); 2.712 (0.8); 2.676 (0.9); 2.672 (1.1); 2.668 (0.8); 2.617 (0.5); 2.542 (197.6); 2.508 (148.4); 2.503 (187.9); 2.499 (137.1); 2.437 (0.6); 2.410 (0.3); 2.392 (0.3); 2.368 (1.0); 2.335 (1.1); 2.330 (1.3); 2.075 (0.5); 1.234 (0.5); 0.000 (3.6) |
Example I-27: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 9.209 (1.5); 8.815 (0.5); 8.675 (2.5); 8.584 (1.9); 8.575 (0.4); 8.315 (1.2); 8.300 (2.2); 8.240 (5.3); 8.155 (7.1); 8.138 (3.1); 8.076 (1.6); 7.932 (2.4); 7.797 (0.5); 7.772 (0.5); 7.745 (0.5); 7.725 (0.4); 7.667 (7.5); 7.648 (10.7); 7.630 (3.4); 7.619 (4.8); 7.600 (8.8); 7.580 (6.3); 7.500 (0.5); 7.485 (2.3); 7.467 (13.1); 7.447 (14.0); 7.428 (4.3); 7.390 (1.7); 7.371 (3.8); 7.350 (3.3); 7.334 (1.0); 7.295 (1.6); 7.274 (3.1); 7.253 (0.5); 7.044 (4.9); 7.026 (4.4); 7.005 (3.9); 6.900 (1.2); 6.646 (3.4); 5.965 (6.2); 5.617 (0.5); 5.603 (0.8); 5.591 (0.4); 5.559 (1.1); 5.547 (2.3); 5.535 (1.1); 4.750 (1.0); 4.714 (2.7); 4.681 (2.8); 4.647 (1.0); 4.426 (1.1); 4.412 (1.0); 4.252 (0.6); 4.241 (0.7); 4.223 (1.4); 4.212 (1.2); 4.171 (1.3); 4.158 (1.3); 4.148 (0.4); 4.142 (0.8); 4.129 (0.7); 4.001 (1.1); 3.968 (2.4); 3.916 (2.6); 3.902 (16.0); 3.882 (1.3); 3.534 (2.1); 3.498 (2.8); 3.329 (381.8); 3.271 (3.6); 3.235 (2.5); 3.176 (1.3); 3.164 (1.2); 2.995 (0.4); 2.672 (2.5); 2.542 (24.3); 2.503 (465.1); 2.368 (0.4); 2.330 (2.7); 1.238 (0.5); 0.002 (50.9); 0.000 (61.7); -0.149 (0.4) |
Example I-28: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.316 (0.7); 8.185 (5.7); 8.159 (16.0); 7.374 (3.1); 7.353 (7.8); 7.326 (8.2); 7.304 (3.2); 6.990 (3.8); 6.986 (3.7); 6.096 (6.6); 4.646 (2.1); 4.611 (3.1); 4.486 (3.0); 4.451 (2.0); 3.451 (2.3); 3.416 (3.0); 3.395 (0.7); 3.332 (682.4); 3.290 (0.6); 3.278 (0.7); 3.176 (2.8); 3.141 (2.2); 2.995 (0.7); 2.671 (1.8); 2.667 (1.3); 2.565 (0.6); 2.542 (53.0); 2.507 (216.5); 2.502 (276.6); 2.498 (201.2); 2.455 (0.5); 2.333 (1.3); 2.329 (1.7); 2.324 (1.2); 1.258 (0.4); 1.235 (1.7); 0.000 (47.2) |
Example I-29: 1H-NMR (400.0 MHz, CD3CN): |
δ= 8.196 (5.4); 8.191 (5.8); 8.184 (5.6); 8.179 (5.5); 8.114 (16.0); 7.835 (0.4); 7.726 (16.0); 7.625 (5.2); 7.621 (5.2); 7.606 (5.7); 7.602 (5.5); 7.209 (5.6); 7.203 (5.7); 7.192 (6.1); 7.180 (9.2); 7.174 (11.0); 7.162 (5.4); 7.145 (5.2); 7.124 (11.1); 7.102 (6.9); 7.002 (6.1); 6.997 (5.8); 6.981 (4.4); 6.976 (4.2); 5.448 (5.8); 5.014 (7.3); 4.978 (8.6); 4.711 (12.3); 4.563 (8.6); 4.527 (7.4); 4.068 (0.6); 4.050 (0.5); 3.463 (4.4); 3.427 (10.8); 3.382 (12.8); 3.346 (5.2); 3.043 (0.6); 2.818 (0.6); 2.469 (0.5); 2.465 (0.7); 2.460 (0.5); 2.160 (102.2); 2.132 (0.4); 2.126 (0.4); 2.120 (0.5); 2.114 (0.8); 2.107 (1.0); 2.101 (0.7); 2.095 (0.4); 1.972 (2.6); 1.964 (10.0); 1.958 (15.3); 1.952 (69.0); 1.946 (120.8); 1.940 (159.1); 1.934 (108.6); 1.928 (55.6); 1.781 (0.4); 1.775 (0.7); 1.768 (0.9); 1.762 (0.6); 1.756 (0.3); 1.371 (0.7); 1.340 (0.6); 1.322 (0.4); 1.285 (1.0); 1.276 (2.0); 1.270 (1.7); 1.221 (0.6); 1.204 (1.1); 1.186 (0.7); 0.983 (0.3); 0.882 (0.5); 0.146 (0.5); 0.008 (3.7); 0.000 (112.6); -0.009 (3.8); -0.150 (0.5) |
Example I-30: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.446 (10.0); 8.316 (16.0); 8.304 (6.5); 7.784 (11.3); 7.301 (4.9); 7.289 (4.8); 7.206 (1.3); 7.200 (1.3); 7.183 (1.4); 7.176 (2.8); 7.169 (1.5); 7.157 (1.6); 7.152 (3.2); 7.147 (1.6); 7.134 (2.2); 7.129 (1.4); 7.112 (1.2); 6.874 (1.2); 6.868 (1.2); 6.853 (2.2); 6.847 (2.0); 6.832 (1.1); 6.826 (1.0); 6.149 (11.0); 4.828 (3.2); 4.792 (4.2); 4.618 (3.9); 4.583 (2.8); 3.493 (2.7); 3.458 (3.5); 3.328 (74.6); 3.271 (4.0); 3.236 (3.0); 2.672 (0.3); 2.542 (38.0); 2.525 (0.9); 2.511 (20.2); 2.507 (40.2); 2.503 (52.4); 2.498 (37.1); 2.493 (17.3); 2.329 (0.3); 0.000 (2.4) |
Example I-31: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.510 (1.1); 8.308 (7.9); 8.304 (7.8); 8.248 (15.9); 8.191 (5.0); 8.189 (4.8); 8.179 (5.1); 8.177 (4.9); 8.080 (0.9); 8.075 (0.3); 8.058 (1.0); 8.029 (1.0); 7.858 (16.0); 7.696 (1.0); 7.675 (0.9); 7.347 (7.7); 7.343 (2.9); 7.331 (4.1); 7.326 (14.0); 7.320 (2.1); 7.280 (2.4); 7.275 (15.6); 7.270 (3.8); 7.258 (3.0); 7.253 (8.4); 7.247 (0.9); 7.189 (3.1); 7.176 (3.8); 7.173 (3.8); 7.161 (3.0); 5.998 (1.9); 5.903 (15.0); 4.721 (2.4); 4.686 (7.5); 4.661 (7.4); 4.625 (2.4); 3.373 (4.0); 3.341 (40.4); 3.102 (4.5); 3.067 (3.6); 3.000 (0.4); 2.714 (0.5); 2.544 (103.1); 2.527 (0.4); 2.514 (7.4); 2.509 (15.1); 2.505 (19.7); 2.500 (14.0); 2.495 (6.5); 2.370 (0.5); 0.008 (0.3); 0.000 (8.7) |
Example I-32: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.392 (0.7); 8.369 (0.3); 8.315 (0.4); 8.244 (13.2); 8.191 (8.8); 8.163 (0.4); 7.967 (0.6); 7.874 (13.0); 7.379 (4.3); 7.365 (5.5); 7.357 (6.0); 7.344 (5.1); 7.303 (0.4); 7.242 (5.9); 7.229 (5.7); 7.080 (5.1); 7.058 (9.4); 7.035 (4.5); 6.976 (0.3); 6.856 (0.4); 5.912 (13.1); 4.705 (0.4); 4.668 (16.0); 4.633 (0.4); 3.450 (0.5); 3.437 (0.6); 3.413 (0.8); 3.395 (1.4); 3.333 (1364.6); 3.285 (2.4); 3.267 (1.1); 3.257 (1.2); 3.246 (1.0); 3.225 (0.5); 3.210 (0.5); 3.204 (0.5); 3.194 (0.5); 3.138 (0.4); 3.083 (4.5); 3.049 (3.6); 2.995 (1.1); 2.712 (0.6); 2.671 (2.8); 2.667 (2.0); 2.541 (105.6); 2.506 (336.3); 2.502 (419.6); 2.498 (309.4); 2.367 (0.8); 2.329 (2.7); 1.259 (0.4); 1.234 (0.9); 0.000 (15.0) |
Example I-33: 1H-NMR (400.0 MHz, CD3CN): |
δ= 8.441 (5.8); 8.340 (0.3); 8.319 (0.3); 8.277 (0.4); 8.266 (0.4); 8.235 (3.8); 8.223 (3.9); 8.208 (0.4); 8.195 (0.4); 8.158 (0.4); 8.130 (0.3); 8.111 (0.3); 8.095 (0.4); 8.083 (0.4); 8.054 (5.6); 8.039 (0.5); 8.007 (0.3); 7.996 (0.3); 7.960 (1.7); 7.822 (5.2); 7.399 (2.4); 7.395 (3.2); 7.390 (1.1); 7.378 (4.6); 7.375 (4.0); 7.369 (0.5); 7.321 (1.3); 7.316 (1.7); 7.311 (0.8); 7.300 (4.3); 7.296 (1.7); 7.281 (3.1); 7.274 (1.7); 7.270 (2.3); 7.267 (1.2); 7.260 (0.7); 7.253 (1.8); 7.244 (0.3); 7.238 (0.4); 7.235 (0.5); 7.163 (3.1); 7.151 (3.0); 4.761 (2.7); 4.725 (4.4); 4.610 (4.4); 4.595 (3.1); 4.574 (2.7); 3.432 (2.0); 3.396 (4.3); 3.342 (4.5); 3.306 (2.1); 2.920 (16.0); 2.805 (14.2); 2.250 (16.6); 2.002 (0.5); 1.995 (1.0); 1.988 (1.8); 1.983 (8.0); 1.976 (14.1); 1.970 (18.4); 1.964 (12.6); 1.958 (6.4) |
Example I-34: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.503 (9.2); 8.200 (2.8); 8.184 (7.8); 8.091 (7.2); 8.069 (7.8); 8.014 (9.0); 7.508 (3.1); 7.503 (1.5); 7.487 (5.8); 7.468 (4.5); 7.402 (1.2); 7.381 (2.2); 7.362 (4.0); 7.340 (2.7); 7.296 (2.1); 7.278 (3.4); 7.259 (1.4); 7.169 (6.2); 7.147 (5.7); 7.127 (2.3); 7.120 (7.8); 7.098 (7.6); 7.091 (1.2); 6.940 (4.0); 6.919 (4.4); 6.897 (2.6); 5.968 (3.4); 5.942 (16.0); 4.628 (0.9); 4.593 (1.4); 4.508 (1.4); 4.472 (0.9); 3.425 (1.0); 3.390 (1.4); 3.374 (0.4); 3.332 (222.2); 3.180 (1.3); 3.146 (1.0); 2.996 (0.4); 2.956 (0.5); 2.711 (0.4); 2.671 (0.7); 2.542 (81.3); 2.506 (80.9); 2.502 (107.3); 2.498 (81.1); 2.367 (0.4); 2.329 (0.7); 2.324 (0.5); 1.235 (0.4); 0.007 (1.1); 0.000 (24.6); -0.008 (1.2) |
Example I-35: 1H-NMR (400.0 MHz, CD3CN): |
δ= 15.359 (0.5); 14.322 (0.5); 12.810 (0.6); 12.262 (0.6); 12.167 (1.1); 12.142 (1.1); 12.127 (1.2); 12.121 (1.0); 12.092 (1.0); 12.086 (1.0); 12.037 (1.0); 12.014 (1.0); 11.962 (1.6); 11.914 (1.0); 11.854 (0.9); 11.773 (1.1); 8.354 (0.9); 8.297 (6.1); 8.233 (1.0); 8.228 (0.9); 8.220 (0.9); 8.213 (0.7); 8.206 (0.9); 8.186 (5.0); 8.181 (4.8); 8.175 (4.7); 8.170 (4.6); 8.072 (13.8); 8.046 (0.6); 8.021 (0.7); 8.009 (0.8); 8.003 (0.8); 7.988 (0.9); 7.910 (5.8); 7.831 (0.6); 7.825 (0.6); 7.771 (12.7); 7.621 (10.3); 7.599 (14.7); 7.585 (0.6); 7.556 (4.5); 7.552 (4.1); 7.537 (5.0); 7.532 (4.6); 7.514 (16.0); 7.493 (9.7); 7.162 (4.5); 7.150 (4.8); 7.142 (4.3); 7.131 (4.0); 4.811 (6.4); 4.775 (9.3); 4.651 (14.6); 4.606 (9.1); 4.570 (6.4); 4.274 (0.5); 3.393 (3.4); 3.357 (10.5); 3.326 (10.8); 3.290 (3.3); 2.889 (1.2); 2.772 (0.9); 2.726 (0.6); 2.468 (0.9); 2.464 (1.1); 2.265 (0.5); 2.235 (0.6); 2.141 (465.3); 2.120 (3.5); 2.113 (4.8); 2.107 (5.8); 2.101 (3.8); 2.095 (2.1); 2.084 (0.7); 2.074 (0.6); 2.048 (0.7); 2.032 (0.7); 2.023 (0.9); 1.964 (63.8); 1.958 (116.2); 1.952 (405.2); 1.946 (687.0); 1.940 (860.7); 1.934 (587.0); 1.928 (296.9); 1.781 (2.2); 1.774 (3.9); 1.768 (4.9); 1.762 (3.4); 1.756 (1.6); 1.342 (0.6); 1.285 (0.8); 1.272 (1.0); 1.248 (0.5); 1.204 (0.9); 1.186 (0.6); 1.123 (0.6); 0.847 (0.6); 0.146 (2.0); 0.000 (454.6); - 0.008 (18.5); -0.149 (2.1); -0.312 (0.5) |
Example I-36: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.277 (7.4); 8.273 (7.2); 8.211 (14.6); 8.154 (4.6); 8.153 (4.6); 8.142 (4.7); 8.140 (4.6); 7.875 (14.6); 7.339 (4.6); 7.335 (6.1); 7.318 (8.2); 7.241 (2.3); 7.237 (3.3); 7.232 (1.4); 7.220 (8.4); 7.201 (5.9); 7.192 (2.6); 7.188 (4.3); 7.185 (2.5); 7.177 (1.4); 7.171 (4.0); 7.160 (3.2); 7.152 (1.6); 7.147 (3.8); 7.145 (3.7); 7.132 (2.9); 5.787 (15.1); 4.688 (0.3); 4.652 (16.0); 4.616 (0.3); 3.349 (4.1); 3.336 (39.0); 3.315 (4.7); 3.090 (4.6); 3.055 (3.6); 2.542 (56.3); 2.525 (0.4); 2.512 (8.5); 2.507 (17.1); 2.503 (22.2); 2.498 (15.7); 2.494 (7.3); 0.000 (7.4) |
Example I-37: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.161 (15.7); 8.128 (6.8); 8.115 (6.9); 7.882 (16.0); 7.354 (4.9); 7.350 (6.8); 7.345 (2.1); 7.333 (9.6); 7.278 (3.0); 7.275 (4.5); 7.270 (1.7); 7.257 (9.5); 7.253 (3.9); 7.238 (5.5); 7.217 (2.5); 7.214 (4.2); 7.211 (2.4); 7.202 (1.5); 7.197 (4.8); 7.190 (0.9); 7.182 (0.9); 7.179 (1.3); 7.176 (0.7); 7.109 (8.4); 7.017 (4.9); 7.014 (4.5); 7.005 (4.7); 7.001 (4.3); 5.809 (16.0); 4.610 (2.5); 4.575 (8.2); 4.551 (8.1); 4.516 (2.5); 3.341 (71.8); 3.273 (3.9); 3.239 (5.8); 3.127 (5.7); 3.093 (3.8); 3.004 (0.5); 2.719 (0.4); 2.549 (101.4); 2.537 (0.4); 2.532 (0.8); 2.519 (15.3); 2.514 (30.0); 2.510 (38.4); 2.505 (27.0); 2.501 (12.4); 2.375 (0.4); 2.082 (0.3) |
Example I-38: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.410 (1.7); 8.285 (1.9); 8.275 (1.0); 8.263 (1.0); 7.948 (1.2); 7.926 (1.4); 7.863 (1.9); 7.594 (1.3); 7.573 (1.2); 7.277 (0.8); 7.264 (0.8); 6.081 (1.6); 4.761 (0.8); 4.743 (0.8); 3.540 (0.5); 3.504 (0.6); 3.392 (0.3); 3.353 (90.5); 3.351 (89.6); 3.274 (0.6); 3.238 (0.5); 2.544 (20.0); 2.526 (0.4); 2.513 (8.0); 2.509 (16.1); 2.504 (21.2); 2.500 (15.5); 1.361 (16.0); 0.000 (1.4) |
Example I-39: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.547 (7.5); 8.220 (14.9); 8.163 (5.4); 8.155 (7.0); 8.141 (12.6); 8.049 (7.6); 7.932 (6.3); 7.927 (1.9); 7.914 (2.0); 7.910 (5.4); 7.901 (16.0); 7.814 (3.1); 7.811 (4.3); 7.806 (1.1); 7.793 (4.5); 7.785 (0.6); 7.734 (0.3); 7.713 (0.3); 7.676 (5.9); 7.673 (7.7); 7.668 (2.2); 7.655 (8.8); 7.600 (8.9); 7.579 (11.7); 7.558 (1.5); 7.556 (2.2); 7.551 (0.9); 7.538 (5.0); 7.534 (2.5); 7.519 (3.3); 7.484 (1.5); 7.481 (2.5); 7.478 (2.6); 7.473 (4.8); 7.469 (2.5); 7.463 (3.6); 7.455 (11.4); 7.450 (13.2); 7.445 (4.9); 7.435 (7.2); 7.428 (8.8); 7.377 (2.2); 7.374 (3.6); 7.371 (2.1); 7.360 (1.7); 7.355 (4.8); 7.351 (1.3); 7.340 (1.2); 7.337 (1.8); 7.334 (1.0); 7.177 (8.1); 7.082 (4.5); 7.079 (4.2); 7.069 (4.4); 7.066 (4.1); 6.042 (12.3); 5.882 (13.7); 4.657 (2.8); 4.621 (6.1); 4.578 (6.1); 4.542 (2.8); 3.347 (35.7); 3.316 (3.3); 3.282 (4.8); 3.173 (4.7); 3.139 (3.2); 3.006 (1.7); 2.719 (0.7); 2.569 (0.6); 2.549 (169.9); 2.532 (0.8); 2.519 (12.3); 2.514 (25.4); 2.510 (33.4); 2.505 (23.4); 2.501 (10.9); 2.375 (0.7); 2.082 (1.5) |
Example I-40: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.314 (0.7); 8.288 (0.5); 8.264 (3.5); 8.200 (10.8); 7.876 (4.0); 7.385 (0.4); 7.363 (7.2); 7.341 (14.2); 7.301 (16.0); 7.279 (8.2); 7.271 (7.3); 7.258 (6.7); 5.959 (13.8); 4.711 (0.6); 4.673 (9.1); 4.635 (0.6); 4.099 (0.5); 4.085 (0.5); 3.902 (11.8); 3.373 (4.6); 3.327 (198.3); 3.267 (0.6); 3.219 (0.4); 3.175 (2.7); 3.163 (2.6); 3.093 (4.6); 3.059 (3.7); 2.676 (1.3); 2.672 (1.7); 2.667 (1.3); 2.542 (3.1); 2.524 (4.9); 2.507 (223.0); 2.502 (309.8); 2.498 (236.5); 2.334 (1.3); 2.329 (1.7); 2.325 (1.3); 1.234 (0.4); 0.008 (2.0); 0.000 (59.1); -0.008 (2.3) |
Example I-41: 1H-NMR (300.2 MHz, d6-DMSO): |
δ= 8.510 (0.6); 8.343 (15.7); 8.213 (10.6); 8.043 (0.4); 7.818 (16.0); 7.257 (2.0); 7.249 (2.4); 7.217 (5.5); 7.191 (4.0); 7.186 (3.9); 7.162 (2.0); 7.121 (8.0); 7.115 (7.9); 6.938 (1.9); 6.929 (2.0); 6.910 (3.4); 6.902 (3.2); 6.882 (1.7); 6.874 (1.6); 6.246 (15.9); 5.842 (0.5); 5.832 (0.5); 4.852 (4.3); 4.805 (6.3); 4.654 (5.9); 4.606 (3.9); 4.088 (0.7); 4.064 (2.0); 4.040 (2.0); 4.016 (0.7); 3.551 (3.8); 3.504 (5.4); 3.409 (0.5); 3.342 (106.6); 3.287 (4.4); 2.530 (40.0); 2.524 (53.9); 2.518 (39.5); 2.513 (19.1); 2.012 (8.9); 1.932 (0.5); 1.270 (1.3); 1.221 (2.4); 1.198 (4.7); 1.174 (2.4); 0.896 (0.4); 0.881 (1.0); 0.860 (0.5); 0.034 (2.8); 0.023 (61.9); 0.012 (2.7) |
Example I-42: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.487 (13.2); 8.305 (16.0); 8.300 (9.0); 8.288 (8.6); 7.761 (15.2); 7.561 (8.8); 7.555 (8.9); 7.365 (6.5); 7.344 (9.3); 7.252 (6.0); 7.246 (5.9); 7.241 (6.7); 7.228 (7.6); 7.206 (0.4); 6.214 (13.5); 6.205 (0.3); 5.325 (0.6); 5.187 (5.0); 5.151 (5.7); 4.669 (5.3); 4.633 (4.9); 3.898 (0.3); 3.749 (4.5); 3.714 (5.4); 3.682 (0.3); 3.657 (0.3); 3.638 (0.3); 3.629 (0.4); 3.617 (0.5); 3.606 (0.4); 3.567 (0.4); 3.547 (0.5); 3.532 (0.5); 3.509 (0.5); 3.503 (0.5); 3.498 (0.6); 3.479 (0.6); 3.461 (5.9); 3.445 (1.0); 3.425 (5.1); 3.402 (1.9); 3.395 (2.3); 3.389 (2.3); 3.380 (4.4); 3.336 (2969.6); 3.299 (4.1); 3.287 (2.6); 3.259 (1.4); 3.233 (0.8); 3.222 (0.6); 3.210 (0.4); 3.197 (0.5); 3.186 (0.5); 3.150 (0.4); 3.092 (0.3); 2.995 (1.3); 2.711 (0.6); 2.676 (3.4); 2.671 (4.6); 2.667 (3.3); 2.662 (1.6); 2.541 (109.2); 2.525 (12.0); 2.511 (277.1); 2.507 (556.6); 2.502 (723.9); 2.498 (511.4); 2.493 (237.9); 2.464 (1.2); 2.429 (0.5); 2.424 (0.5); 2.367 (0.4); 2.333 (3.3); 2.329 (4.4); 2.324 (3.3); 2.320 (1.6); 2.282 (0.5); 2.026 (0.5); 2.008 (1.0); 1.989 (1.0); 1.977 (0.5); 1.958 (0.4); 1.495 (0.3); 1.475 (0.4); 1.454 (0.4); 1.437 (0.3); 1.313 (0.5); 1.298 (0.9); 1.235 (10.8); 1.209 (2.8); 1.193 (2.7); 0.870 (0.7); 0.854 (2.0); 0.837 (0.8); 0.008 (0.5); 0.000 (11.7) |
Example I-43: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.489 (0.3); 8.312 (16.0); 8.212 (3.5); 8.200 (3.6); 8.199 (3.5); 8.021 (0.4); 7.776 (11.1); 7.226 (1.3); 7.219 (1.3); 7.204 (3.2); 7.192 (3.5); 7.189 (4.1); 7.176 (2.5); 7.166 (1.3); 7.089 (1.0); 7.071 (1.3); 7.066 (2.1); 7.049 (2.1); 7.044 (1.4); 7.026 (1.1); 6.823 (1.2); 6.817 (1.2); 6.802 (2.1); 6.796 (2.0); 6.780 (1.0); 6.774 (1.0); 6.123 (11.2); 5.810 (0.3); 4.811 (3.0); 4.775 (4.2); 4.644 (4.1); 4.608 (2.8); 3.449 (2.6); 3.414 (3.1); 3.381 (0.3); 3.362 (1.2); 3.332 (587.9); 3.298 (0.6); 3.286 (0.5); 3.101 (3.2); 3.067 (2.7); 3.054 (0.6); 2.995 (0.8); 2.711 (0.4); 2.676 (0.7); 2.671 (1.0); 2.667 (0.7); 2.663 (0.4); 2.541 (120.5); 2.525 (2.6); 2.511 (60.5); 2.507 (122.6); 2.502 (160.6); 2.498 (115.0); 2.493 (54.7); 2.368 (0.5); 2.333 (0.8); 2.329 (1.0); 2.324 (0.7); 0.008 (0.6); 0.000 (16.2); -0.009 (0.5) |
Example I-44: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.311 (15.2); 8.156 (7.2); 8.143 (7.4); 7.804 (16.0); 7.251 (1.7); 7.244 (1.7); 7.228 (1.9); 7.221 (3.0); 7.214 (1.8); 7.197 (1.7); 7.191 (1.6); 7.146 (9.1); 7.125 (1.8); 7.119 (3.0); 7.102 (3.1); 7.097 (2.0); 7.079 (1.6); 7.017 (4.8); 7.014 (4.6); 7.004 (4.7); 7.001 (4.5); 6.874 (1.8); 6.867 (1.8); 6.852 (3.2); 6.846 (3.0); 6.831 (1.6); 6.825 (1.5); 6.163 (14.1); 4.745 (4.3); 4.710 (6.2); 4.587 (5.9); 4.551 (4.0); 3.358 (13.1); 3.333 (2.9); 3.297 (3.8); 3.131 (5.2); 3.097 (3.8); 3.006 (0.4); 2.719 (0.5); 2.550 (88.2); 2.528 (0.4); 2.519 (3.9); 2.514 (8.0); 2.510 (10.6); 2.505 (7.6); 2.501 (3.6); 2.375 (0.5); 2.081 (0.5) |
Example I-45: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.322 (16.0); 8.218 (9.8); 8.216 (9.8); 7.791 (15.6); 7.307 (6.7); 7.294 (6.7); 7.254 (1.8); 7.248 (1.8); 7.232 (2.1); 7.224 (3.2); 7.218 (2.0); 7.201 (1.9); 7.195 (1.8); 7.126 (1.5); 7.109 (2.0); 7.104 (3.2); 7.086 (3.2); 7.081 (2.2); 7.064 (1.7); 6.869 (1.9); 6.863 (1.9); 6.848 (3.4); 6.842 (3.1); 6.826 (1.7); 6.820 (1.5); 6.187 (15.6); 4.797 (4.2); 4.761 (6.3); 4.644 (6.1); 4.608 (4.0); 3.447 (4.1); 3.413 (4.8); 3.363 (0.9); 3.332 (273.8); 3.289 (0.4); 3.279 (0.4); 3.104 (4.9); 3.069 (4.0); 2.996 (1.1); 2.712 (0.3); 2.676 (0.5); 2.672 (0.7); 2.667 (0.5); 2.542 (83.4); 2.511 (44.9); 2.507 (84.3); 2.503 (106.7); 2.498 (77.4); 2.368 (0.4); 2.334 (0.5); 2.329 (0.7); 2.325 (0.5); 0.000 (16.9); -0.008 (0.8) |
Example I-46: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.286 (11.6); 8.059 (6.0); 8.046 (6.2); 7.919 (12.0); 7.394 (4.2); 7.373 (8.0); 7.354 (12.4); 7.332 (8.9); 7.227 (2.9); 7.215 (5.4); 7.202 (2.8); 7.132 (2.6); 7.114 (4.4); 7.095 (2.0); 6.948 (0.4); 6.921 (8.7); 6.902 (16.0); 6.880 (8.8); 5.879 (10.1); 4.761 (1.7); 4.725 (6.4); 4.706 (6.4); 4.671 (1.7); 3.381 (4.4); 3.365 (30.0); 3.348 (4.5); 3.125 (4.0); 3.091 (3.2); 2.718 (0.5); 2.549 (88.2); 2.513 (8.4); 2.509 (11.4); 2.505 (9.2); 2.374 (0.5); 0.000 (2.5) |
Example I-47: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.201 (14.9); 8.159 (6.6); 8.146 (6.8); 7.862 (15.3); 7.362 (6.2); 7.357 (2.4); 7.346 (3.6); 7.341 (15.1); 7.336 (2.6); 7.311 (15.6); 7.305 (3.4); 7.294 (2.3); 7.289 (6.4); 7.166 (8.0); 7.031 (4.4); 7.028 (4.2); 7.018 (4.2); 7.015 (4.0); 5.928 (16.0); 4.643 (3.6); 4.608 (6.2); 4.531 (6.1); 4.496 (3.6); 3.345 (29.6); 3.283 (3.5); 3.249 (5.3); 3.155 (5.2); 3.121 (3.3); 3.005 (0.5); 2.719 (0.5); 2.550 (95.6); 2.533 (0.4); 2.527 (0.6); 2.519 (7.5); 2.514 (15.5); 2.510 (20.5); 2.505 (14.6); 2.501 (6.9); 2.375 (0.5); 2.082 (0.4) |
Example I-48: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.224 (16.0); 8.171 (11.4); 7.888 (15.4); 7.351 (7.9); 7.333 (11.5); 7.266 (4.5); 7.249 (10.7); 7.230 (7.4); 7.215 (5.4); 7.194 (9.2); 7.181 (8.3); 5.846 (15.6); 4.702 (2.7); 4.666 (9.5); 4.644 (9.5); 4.609 (2.6); 3.389 (0.4); 3.351 (7.3); 3.332 (228.1); 3.317 (9.3); 3.085 (6.0); 3.051 (4.7); 2.995 (0.6); 2.712 (0.5); 2.671 (0.7); 2.542 (114.5); 2.506 (82.9); 2.502 (103.6); 2.498 (78.6); 2.368 (0.6); 2.329 (0.7); 0.000 (4.6) |
Example I-49: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.773 (0.4); 8.226 (15.7); 8.118 (0.4); 7.999 (9.0); 7.987 (9.2); 7.886 (16.0); 7.521 (0.4); 7.500 (0.4); 7.347 (7.6); 7.329 (10.4); 7.260 (4.2); 7.243 (10.3); 7.224 (7.4); 7.212 (5.4); 7.202 (1.8); 7.195 (4.5); 7.187 (1.0); 7.177 (1.3); 7.142 (4.0); 7.130 (7.4); 7.117 (3.8); 5.851 (13.6); 4.715 (2.2); 4.679 (9.5); 4.663 (9.5); 4.627 (2.2); 3.389 (4.6); 3.350 (53.7); 3.149 (5.6); 3.115 (4.3); 2.714 (0.5); 2.568 (0.4); 2.561 (1.0); 2.545 (102.8); 2.531 (1.6); 2.522 (1.2); 2.510 (16.9); 2.505 (23.0); 2.501 (18.1); 2.371 (0.5); 0.000 (6.8) |
Example I-50: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.310 (16.0); 8.200 (1.2); 8.187 (1.2); 8.152 (7.0); 8.140 (7.2); 7.788 (16.0); 7.754 (1.3); 7.749 (1.3); 7.664 (0.7); 7.643 (0.9); 7.584 (8.2); 7.578 (8.3); 7.543 (0.7); 7.538 (0.7); 7.528 (0.9); 7.523 (0.8); 7.507 (0.9); 7.502 (0.9); 7.468 (0.7); 7.463 (0.7); 7.356 (0.6); 7.351 (0.7); 7.349 (0.6); 7.343 (0.5); 7.333 (1.7); 7.328 (0.5); 7.321 (1.1); 7.312 (1.4); 7.300 (0.6); 7.283 (6.7); 7.261 (11.4); 7.253 (1.2); 7.249 (0.9); 7.242 (0.8); 7.237 (0.8); 7.232 (0.9); 7.206 (6.5); 7.200 (6.1); 7.184 (3.9); 7.178 (4.2); 7.169 (8.9); 7.110 (1.6); 7.107 (1.4); 7.069 (0.5); 7.064 (0.4); 7.048 (0.4); 7.043 (0.4); 7.028 (4.9); 7.025 (4.7); 7.016 (4.8); 7.012 (4.6); 6.994 (1.4); 6.839 (1.3); 6.820 (0.8); 6.816 (0.8); 6.806 (0.8); 6.803 (0.8); 6.259 (12.4); 5.761 (1.6); 5.081 (5.2); 5.045 (6.0); 4.705 (6.0); 4.669 (5.1); 4.193 (1.1); 3.776 (4.9); 3.741 (5.3); 3.344 (19.3); 3.155 (5.0); 3.120 (4.5); 3.005 (0.6); 2.990 (0.5); 2.977 (0.5); 2.719 (0.7); 2.550 (155.4); 2.533 (0.9); 2.519 (12.2); 2.515 (24.9); 2.510 (32.9); 2.505 (23.7); 2.501 (11.4); 2.375 (0.7); 2.082 (0.5) |
Example I-51: 1H-NMR (400.0 MHz, CD3CN): |
δ= 8.164 (4.3); 8.159 (4.4); 8.152 (4.5); 8.147 (4.3); 8.017 (13.3); 7.925 (0.8); 7.780 (13.2); 7.546 (4.4); 7.541 (4.3); 7.527 (4.8); 7.522 (4.6); 7.359 (5.8); 7.355 (7.9); 7.350 (2.7); 7.343 (5.5); 7.338 (11.2); 7.335 (10.3); 7.329 (1.4); 7.287 (3.2); 7.282 (4.3); 7.277 (2.0); 7.265 (11.4); 7.262 (4.1); 7.250 (3.8); 7.247 (7.0); 7.239 (4.0); 7.235 (6.2); 7.232 (3.3); 7.225 (1.8); 7.218 (4.6); 7.210 (0.8); 7.204 (0.8); 7.200 (1.2); 7.197 (0.6); 7.129 (5.2); 7.117 (5.1); 7.110 (4.8); 7.098 (4.6); 5.447 (3.3); 4.761 (7.2); 4.726 (10.2); 4.559 (10.2); 4.523 (7.3); 4.460 (16.0); 3.454 (0.3); 3.369 (3.2); 3.333 (11.3); 3.307 (11.6); 3.271 (3.3); 2.888 (10.6); 2.772 (8.6); 2.771 (8.8); 2.139 (49.1); 2.119 (0.4); 2.113 (0.6); 2.107 (0.8); 2.101 (0.6); 1.971 (1.2); 1.964 (8.6); 1.958 (13.3); 1.952 (54.2); 1.946 (94.0); 1.939 (121.2); 1.933 (82.6); 1.927 (41.8); 1.914 (0.4); 1.774 (0.5); 1.768 (0.7); 1.762 (0.5); 1.285 (0.4); 1.270 (0.4); 0.000 (4.8) |
Example I-52: 1H-NMR (400.0 MHz, CD3CN): |
δ= 8.295 (1.0); 8.179 (2.8); 8.174 (2.9); 8.168 (2.9); 8.163 (2.8); 8.134 (0.3); 8.060 (8.6); 7.926 (1.6); 7.910 (1.0); 7.784 (8.4); 7.572 (2.8); 7.567 (2.7); 7.553 (3.0); 7.548 (2.9); 7.333 (0.9); 7.327 (5.9); 7.321 (2.5); 7.310 (3.3); 7.305 (13.2); 7.299 (1.9); 7.274 (2.0); 7.268 (12.8); 7.263 (2.9); 7.252 (2.2); 7.246 (5.6); 7.240 (0.7); 7.158 (3.5); 7.146 (3.3); 7.139 (3.1); 7.127 (2.9); 4.757 (4.5); 4.721 (6.4); 4.571 (6.4); 4.553 (6.8); 4.535 (4.4); 3.365 (2.5); 3.329 (6.7); 3.289 (6.8); 3.253 (2.5); 2.889 (16.0); 2.772 (12.8); 2.771 (12.9); 2.473 (0.4); 2.468 (0.8); 2.464 (1.1); 2.459 (0.8); 2.454 (0.4); 2.153 (191.7); 2.120 (1.2); 2.113 (1.6); 2.107 (2.0); 2.101 (1.4); 2.095 (0.7); 1.972 (2.1); 1.964 (21.1); 1.958 (31.7); 1.952 (145.5); 1.946 (255.5); 1.940 (333.2); 1.934 (227.8); 1.928 (116.3); 1.915 (1.4); 1.781 (0.7); 1.774 (1.4); 1.768 (1.9); 1.762 (1.3); 1.756 (0.7); 1.713 (1.9); 1.479 (0.4); 1.461 (0.4); 1.277 (0.5); 1.204 (0.5); 0.146 (1.0); 0.008 (7.9); 0.000 (246.3); -0.009 (7.4); - 0.150 (0.9) |
Example I-53: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.347 (7.8); 8.343 (7.8); 8.306 (16.0); 8.201 (4.9); 8.199 (4.7); 8.188 (5.0); 8.186 (4.9); 7.757 (15.8); 7.567 (9.1); 7.561 (9.2); 7.255 (6.1); 7.233 (10.4); 7.179 (6.5); 7.173 (6.2); 7.165 (3.3); 7.157 (4.4); 7.152 (7.4); 7.136 (3.1); 6.201 (14.8); 5.209 (5.1); 5.173 (5.7); 4.727 (5.5); 4.691 (4.8); 3.792 (4.2); 3.757 (4.6); 3.332 (54.9); 3.226 (4.5); 3.192 (4.0); 2.543 (53.5); 2.526 (0.6); 2.521 (0.9); 2.512 (13.8); 2.508 (28.2); 2.503 (37.1); 2.499 (26.4); 2.494 (12.5); 0.008 (0.5); 0.000 (13.8); -0.009 (0.4) |
Example I-54: 1H-NMR (400.0 MHz, d6-DMSO): |
δ= 8.621 (3.1); 8.314 (1.1); 8.282 (2.8); 8.231 (6.6); 8.151 (9.3); 8.103 (3.6); 7.927 (3.2); 7.508 (1.0); 7.499 (1.2); 7.490 (1.7); 7.482 (2.4); 7.468 (2.1); 7.461 (3.0); 7.439 (1.6); 7.432 (1.6); 7.346 (7.1); 7.324 (7.9); 7.284 (0.8); 7.270 (1.0); 7.261 (1.8); 7.247 (1.9); 7.238 (1.3); 7.224 (2.0); 7.210 (1.3); 7.201 (2.6); 7.187 (2.6); 7.178 (2.1); 7.164 (2.2); 7.150 (2.3); 7.139 (2.7); 7.129 (3.0); 7.119 (2.6); 7.107 (1.3); 7.045 (0.4); 7.023 (0.4); 6.989 (6.0); 6.925 (2.3); 6.902 (8.0); 6.884 (8.2); 6.862 (2.9); 6.851 (8.0); 6.829 (7.5); 6.644 (3.9); 5.898 (9.3); 5.519 (1.4); 5.507 (3.1); 5.495 (1.4); 4.728 (1.6); 4.693 (3.2); 4.637 (3.3); 4.602 (1.6); 4.184 (0.7); 4.173 (0.9); 4.155 (1.7); 4.144 (1.6); 4.111 (1.6); 4.098 (1.9); 4.082 (1.0); 4.069 (0.8); 3.919 (1.1); 3.902 (16.0); 3.886 (3.4); 3.861 (3.3); 3.827 (1.2); 3.508 (0.4); 3.447 (3.0); 3.411 (4.1); 3.328 (519.6); 3.257 (0.8); 3.211 (3.8); 3.176 (4.5); 3.163 (1.9); 2.995 (0.4); 2.672 (3.1); 2.542 (27.4); 2.507 (426.9); 2.503 (579.3); 2.499 (465.0); 2.398 (0.5); 2.392 (0.5); 2.384 (0.4); 2.368 (0.4); 2.330 (3.3); 1.908 (0.4); 1.260 (0.3); 1.235 (0.5); 0.146 (0.4); 0.000 (83.7); -0.149 (0.4) |
Example I-55: 1H-NMR (499.9 MHz, CDCl3): |
δ= 8.024 (6.4); 8.015 (6.7); 7.945 (9.4); 7.835 (10.0); 7.269 (4.9); 7.254 (1.7); 7.249 (2.8); 7.236 (2.8); 7.230 (1.9); 7.217 (1.7); 7.082 (3.0); 7.073 (5.7); 7.063 (3.1); 6.818 (1.5); 6.813 (1.6); 6.802 (1.6); 6.796 (2.0); 6.794 (2.0); 6.789 (1.8); 6.777 (1.6); 6.772 (1.7); 6.711 (1.4); 6.707 (1.4); 6.695 (2.5); 6.693 (2.3); 6.690 (2.3); 6.678 (1.5); 6.674 (1.4); 5.156 (1.3); 4.973 (4.0); 4.945 (4.5); 4.488 (4.7); 4.460 (4.3); 3.318 (2.1); 3.291 (5.0); 3.253 (5.7); 3.226 (2.6); 2.003 (16.0); 1.993 (0.6); 1.256 (0.5); 0.000 (4.1) |
Example I-56: 1H-NMR (499.9 MHz, CDCl3): |
δ= 8.054 (0.9); 8.027 (6.0); 8.017 (6.2); 7.960 (9.2); 7.843 (9.6); 7.268 (5.2); 7.253 (1.7); 7.247 (2.7); 7.234 (2.7); 7.229 (1.8); 7.216 (1.5); 7.082 (2.8); 7.072 (5.4); 7.063 (2.9); 6.820 (1.4); 6.815 (1.5); 6.803 (1.6); 6.798 (2.0); 6.796 (1.9); 6.791 (1.7); 6.779 (1.5); 6.774 (1.6); 6.713 (1.4); 6.708 (1.4); 6.696 (2.4); 6.694 (2.3); 6.692 (2.3); 6.680 (1.4); 6.675 (1.3); 5.136 (0.3); 5.116 (0.3); 4.975 (4.0); 4.947 (4.5); 4.491 (4.6); 4.464 (4.2); 3.320 (2.2); 3.293 (5.0); 3.254 (5.6); 3.227 (2.6); 2.003 (16.0); 1.256 (0.4); 0.000 (4.3) |
Example I-57: 1H-NMR (300.2 MHz, CDCl3): |
δ= 8.023 (3.3); 8.006 (3.5); 7.870 (5.2); 7.794 (5.1); 7.646 (0.8); 7.367 (0.5); 7.300 (124.9); 7.233 (0.4); 7.167 (0.8); 7.145 (0.8); 7.136 (1.5); 7.115 (1.5); 7.107 (1.0); 7.085 (0.9); 7.058 (1.5); 7.043 (2.7); 7.026 (1.5); 6.949 (0.7); 6.929 (0.9); 6.920 (0.8); 6.901 (0.9); 6.892 (0.9); 6.888 (1.0); 6.879 (0.8); 6.859 (0.8); 6.851 (0.8); 6.783 (0.8); 6.776 (0.7); 6.756 (1.1); 6.751 (1.1); 6.727 (0.6); 6.719 (0.5); 4.965 (1.5); 4.915 (3.6); 4.848 (3.7); 4.797 (1.7); 3.636 (16.0); 3.507 (0.4); 3.461 (3.7); 3.450 (3.7); 3.403 (0.4); 2.997 (1.1); 2.925 (0.9); 1.654 (0.6); 1.587 (106.3); 1.522 (0.5); 1.293 (1.1); 0.893 (0.4); 0.872 (0.3); 0.233 (0.5); 0.108 (2.8); 0.049 (4.4); 0.039 (126.0); 0.028 (4.7); -0.028 (0.5); -0.159 (0.5) |
Example XII-1: 1H-NMR (400.0 MHz, CD3CN): |
δ= 8.488 (0.4); 8.318 (0.3); 8.247 (5.8); 8.242 (5.9); 8.235 (6.3); 8.230 (6.2); 8.223 (0.8); 8.218 (0.8); 8.215 (0.5); 8.210 (0.4); 8.203 (0.8); 8.198 (0.6); 8.191 (0.6); 8.186 (0.6); 7.757 (0.6); 7.752 (0.5); 7.738 (0.7); 7.733 (0.5); 7.674 (5.9); 7.669 (5.7); 7.655 (6.5); 7.650 (6.1); 7.640 (0.5); 7.588 (0.4); 7.357 (0.6); 7.353 (0.4); 7.346 (0.7); 7.339 (0.5); 7.326 (0.9); 7.313 (0.5); 7.294 (0.3); 7.282 (0.8); 7.270 (0.8); 7.263 (7.8); 7.257 (1.1); 7.251 (7.7); 7.244 (7.0); 7.239 (1.0); 7.232 (6.5); 7.227 (0.9); 7.221 (5.4); 7.214 (1.2); 7.208 (7.0); 7.202 (11.5); 7.201 (12.4); 7.194 (1.0); 7.189 (1.3); 7.181 (11.4); 7.178 (8.8); 7.141 (8.8); 7.136 (7.7); 7.126 (1.5); 7.121 (4.5); 7.119 (4.2); 7.115 (4.3); 7.111 (2.0); 7.105 (1.1); 7.093 (0.8); 7.086 (0.8); 7.074 (1.1); 7.069 (0.8); 7.053 (0.5); 7.048 (0.4); 6.106 (0.5); 4.430 (0.5); 4.410 (0.7); 4.391 (0.5); 4.001 (0.5); 3.983 (0.5); 3.577 (0.4); 3.553 (2.0); 3.517 (0.5); 3.494 (7.1); 3.481 (0.7); 3.458 (10.6); 3.315 (10.8); 3.294 (0.5); 3.278 (7.2); 3.225 (1.2); 3.214 (1.2); 3.207 (0.7); 3.196 (0.5); 3.193 (0.8); 3.186 (0.4); 3.183 (0.5); 3.172 (1.1); 3.136 (0.6); 2.938 (12.9); 2.926 (16.0); 2.831 (12.8); 2.819 (10.3); 2.740 (0.9); 2.728 (0.9); 2.710 (0.4); 2.704 (0.4); 2.697 (0.5); 2.690 (0.3); 2.464 (0.4); 2.380 (1.0); 2.157 (69.5); 2.120 (0.4); 2.114 (0.6); 2.108 (0.7); 2.102 (0.5); 1.972 (0.9); 1.965 (7.7); 1.959 (11.7); 1.953 (50.3); 1.947 (87.6); 1.941 (113.1); 1.934 (77.0); 1.928 (39.4); 1.915 (0.6); 1.775 (0.5); 1.769 (0.7); 1.763 (0.5); 1.621 (1.3); 1.584 (0.3); 1.454 (0.9); 1.441 (1.0); 1.436 (1.5); 1.273 (2.5); 1.255 (2.4); 1.249 (0.8); 1.230 (0.5); 1.227 (0.4); 1.045 (1.0); 0.985 (2.2); 0.973 (2.3); 0.008 (2.0); 0.000 (56.0); -0.009 (1.7) |
Example XII-23: 1H-NMR (400.0 MHz, CD3CN): |
δ= 8.242 (3.5); 8.237 (3.7); 8.230 (3.7); 8.225 (3.7); 7.711 (3.7); 7.706 (3.6); 7.692 (4.0); 7.687 (3.9); 7.406 (3.2); 7.402 (5.5); 7.399 (8.4); 7.395 (3.6); 7.358 (0.3); 7.346 (0.4); 7.340 (1.3); 7.335 (3.6); 7.333 (3.4); 7.331 (3.5); 7.324 (8.0); 7.320 (16.0); 7.314 (8.3); 7.309 (6.0); 7.304 (2.8); 7.301 (3.2); 7.297 (2.2); 7.287 (0.4); 7.283 (0.4); 7.251 (4.8); 7.239 (4.7); 7.232 (4.5); 7.220 (4.4); 3.644 (5.8); 3.606 (7.7); 3.373 (7.5); 3.335 (5.6); 3.196 (0.4); 3.012 (0.4); 2.999 (0.4); 2.835 (8.3); 2.823 (11.1); 2.756 (9.8); 2.744 (7.3); 2.464 (0.3); 2.165 (60.0); 2.114 (0.4); 2.108 (0.5); 2.102 (0.4); 1.972 (0.7); 1.965 (4.6); 1.959 (7.0); 1.953 (31.2); 1.947 (54.8); 1.940 (71.9); 1.934 (49.4); 1.928 (25.4); 1.775 (0.3); 1.769 (0.4); 1.621 (1.7); 1.531 (0.5); 1.517 (0.5); 1.503 (0.8); 1.486 (0.8); 1.436 (1.2); 1.239 (0.8); 1.229 (0.5); 1.222 (0.9); 0.927 (0.9); 0.914 (0.8); 0.008 (1.6); 0.000 (44.7); -0.009 (1.6) |
Example XII-24: 1H-NMR (400.0 MHz, CD3CN): |
δ= 8.318 (0.3); 8.239 (2.5); 8.234 (2.6); 8.227 (2.7); 8.222 (2.7); 7.698 (2.6); 7.693 (2.5); 7.679 (2.9); 7.674 (2.8); 7.379 (2.5); 7.377 (2.0); 7.372 (1.4); 7.363 (2.4); 7.356 (15.9); 7.346 (16.0); 7.340 (2.6); 7.331 (1.7); 7.326 (3.0); 7.324 (2.9); 7.306 (0.6); 7.291 (0.7); 7.269 (0.4); 7.266 (0.3); 7.257 (0.7); 7.250 (1.2); 7.244 (3.3); 7.232 (3.2); 7.225 (3.0); 7.213 (2.8); 3.621 (4.0); 3.582 (5.4); 3.371 (5.2); 3.333 (3.9); 3.011 (0.4); 2.999 (0.5); 2.834 (5.7); 2.822 (7.4); 2.815 (0.5); 2.746 (6.6); 2.734 (5.1); 2.143 (26.6); 2.120 (0.3); 2.114 (0.4); 2.107 (0.5); 2.101 (0.3); 1.964 (3.9); 1.958 (6.5); 1.952 (28.4); 1.946 (49.8); 1.940 (65.0); 1.934 (44.5); 1.928 (22.7); 1.768 (0.4); 1.621 (2.1); 1.527 (0.5); 1.514 (0.5); 1.437 (1.4); 1.241 (0.4); 1.223 (0.4); 0.914 (1.0); 0.901 (1.0); 0.008 (2.7); 0.000 (67.0); -0.009 (2.3) |
Example XII-25: 1H-NMR (400.0 MHz, CD3CN): |
δ= 8.323 (0.5); 8.318 (0.6); 8.311 (0.5); 8.306 (0.5); 8.244 (5.5); 8.240 (5.8); 8.233 (5.8); 8.228 (5.7); 7.778 (0.6); 7.716 (5.7); 7.711 (5.7); 7.697 (6.3); 7.692 (6.2); 7.663 (9.7); 7.642 (16.0); 7.611 (0.5); 7.606 (0.5); 7.582 (15.5); 7.561 (9.4); 7.507 (0.5); 7.487 (0.4); 7.355 (0.6); 7.343 (0.6); 7.336 (0.5); 7.324 (0.5); 7.249 (6.9); 7.237 (6.9); 7.230 (6.5); 7.218 (6.2); 5.447 (5.7); 4.140 (0.4); 4.133 (0.5); 4.130 (0.5); 4.123 (0.4); 3.690 (9.1); 3.651 (11.9); 3.601 (0.6); 3.413 (11.6); 3.375 (8.9); 3.196 (0.6); 3.185 (0.7); 3.182 (0.7); 3.172 (0.7); 2.874 (12.6); 2.862 (15.6); 2.771 (14.6); 2.759 (11.6); 2.709 (0.7); 2.703 (0.7); 2.696 (0.7); 2.689 (0.6); 2.138 (11.1); 1.965 (2.6); 1.959 (4.0); 1.953 (16.9); 1.947 (29.4); 1.941 (38.1); 1.934 (26.0); 1.928 (13.4); 1.621 (1.4); 1.551 (0.4); 1.537 (0.4); 1.522 (0.6); 1.504 (0.6); 1.454 (0.6); 1.441 (0.6); 1.271 (0.4); 1.259 (0.7); 1.241 (0.7); 0.910 (0.9); 0.897 (0.9); 0.000 (0.6) |
Example XII-26: 1H-NMR (400.0 MHz, CD3CN): |
δ= 8.246 (3.9); 8.241 (4.2); 8.234 (4.1); 8.229 (4.1); 7.703 (10.9); 7.699 (8.7); 7.694 (5.4); 7.687 (5.8); 7.682 (16.0); 7.555 (14.6); 7.538 (4.7); 7.534 (11.0); 7.248 (4.5); 7.237 (4.5); 7.230 (4.3); 7.218 (4.0); 3.675 (6.2); 3.636 (8.1); 3.403 (8.0); 3.364 (6.1); 2.874 (8.5); 2.862 (10.4); 2.760 (9.6); 2.748 (7.9); 2.464 (0.3); 2.153 (107.8); 2.120 (0.4); 2.114 (0.6); 2.108 (0.7); 2.101 (0.5); 1.964 (5.2); 1.958 (10.4); 1.952 (44.0); 1.946 (77.4); 1.940 (101.9); 1.934 (71.1); 1.928 (37.1); 1.775 (0.5); 1.769 (0.6); 1.762 (0.4); 1.437 (0.6); 1.428 (0.6); 1.218 (0.5); 1.203 (0.5); 0.146 (0.5); 0.008 (5.5); 0.000 (120.2); -0.009 (6.0); -0.150 (0.5) |
Example XII-47: 1H-NMR (300.2 MHz, CDCl3): |
δ= 8.116 (14.3); 8.100 (14.8); 7.300 (14.3); 7.256 (3.2); 7.235 (3.6); 7.229 (5.7); 7.221 (1.1); 7.208 (6.0); 7.199 (3.8); 7.185 (1.2); 7.178 (2.8); 7.150 (6.7); 7.134 (12.8); 7.118 (6.4); 6.886 (0.3); 6.877 (2.7); 6.869 (4.9); 6.864 (2.4); 6.858 (4.5); 6.849 (3.5); 6.841 (7.8); 6.832 (10.7); 6.823 (3.6); 6.813 (3.5); 6.805 (9.2); 6.796 (2.0); 3.841 (0.4); 3.830 (0.3); 3.690 (0.4); 3.663 (0.3); 3.613 (7.3); 3.565 (9.0); 3.166 (9.0); 3.118 (7.3); 3.021 (12.5); 3.004 (15.6); 2.878 (15.4); 2.862 (12.5); 2.771 (0.6); 2.758 (0.6); 1.608 (16.0); 1.304 (1.3); 0.941 (0.5); 0.918 (1.5); 0.895 (0.6); 0.048 (0.5); 0.037 (15.1); 0.026 (0.6) |
Use Examples
Solvent: | 5% | by volume of Dimethyl sulfoxide |
10% | by volume of Acetone | |
Emulsifier: | 1µl | of Tween® 80 per mg of active ingredient |
Solvent: | 5% | by volume of Dimethyl sulfoxide |
10% | by volume of Acetone | |
Emulsifier: | 1 µl | of Tween® 80 per mg of active ingredient |
Solvent: | 5% | by volume of Dimethyl sulfoxide |
10% | by volume of Acetone | |
Emulsifier: | 1µl | of Tween® 80 per mg of active ingredient |
Solvent: | 5% | by volume of Dimethyl sulfoxide |
10% | by volume of Acetone | |
Emulsifier: | 1µl | of Tween® 80 per mg of active ingredient |
Solvent: | 5% | by volume of Dimethyl sulfoxide |
10% | by volume of Acetone | |
Emulsifier: | 1µl | of Tween® 80 per mg of active ingredient |
Solvent: | 5% | by volume of Dimethyl sulfoxide |
10% | by volume of Acetone | |
Emulsifier: | 1µl | of Tween® 80 per mg of active ingredient |
Solvent: | 5% | by volume of Dimethyl sulfoxide |
10% | by volume of Acetone | |
Emulsifier: | 1µl | of Tween® 80 per mg of active ingredient |
Solvent: | 24.5 | parts by weight of acetone |
24.5 | parts by weight of dimethylacetamide | |
Emulsifier: | 1 | part by weight of alkylaryl polyglycol ether |
Solvent: | 24.5 | parts by weight of acetone |
24.5 | parts by weight of dimethylacetamide | |
Emulsifier: | 1 | part by weight of alkylaryl polyglycol ether |
Solvent: | 24.5 | parts by weight of acetone |
24.5 | parts by weight of dimethylacetamide | |
Emulsifier: | 1 | part by weight of alkylaryl polyglycol ether |
Solvent: | 49 | parts by weight of N,N-dimethylacetamide |
Emulsifier: | 1 | part by weight of alkylaryl polyglycol ether |
Solvent: | 49 | parts by weight of N,N-dimethylacetamide |
Emulsifier: | 1 | part by weight of alkylaryl polyglycol ether |
Solvent: | 49 | parts by weight of N,N-dimethylacetamide |
Emulsifier: | 1 | part by weight of alkylaryl polyglycol ether |
R1 represents phenyl or naphthyl; wherein the phenyl or naphthyl may be non-substituted or substituted by one or more group(s) selected from halogen; hydroxyl; cyano; amino; sulfanyl; pentafluoro-λ6-sulfanyl; carboxaldehyde, hydroxycarbonyl, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-cyanoalkyl; C1-C8-alkyloxy; C1-C8-halogenalkyloxy; tri(C1-C8-alkyl)silyl; tri(C1-C8-alkyl)silyl-C1-C8-alkyl; C3-C7-cycloalkyl; C3-C7-halogencycloalkyl; C3-C7-cycloalkenyl; C3-C7-halogencycloalkenyl; C4-C10-cycloalkylalkyl; C4-C10-halocycloalkylalkyl; C6-C12-cycloalkylcycloalkyl; C1-C8-alkyl-C3-C7-cycloalkyl; C1-C8-alkoxy-C3-C7-cycloalkyl; tri(C1-C8-alkyl)silyl-C3-C7-cycloalkyl; C2-C8-alkenyl; C2-C8-alkynyl; C2-C8-alkenyloxy; C2-C8-halogenalkenyloxy; C3-C8-alkynyloxy; C3-C8-halogenoalkynyloxy; C1-C8-alkylamino; C1-C8-halogenalkylamino; C1-C8-cyanoalkoxy; C4-C8-cycloalkylalkoxy; C3-C6-cycloalkoxy; C1-C8-alkylsulfanyl; C1-C8-halogenoalkylsulfanyl; C1-C8-alkylcarbonyl; C1-C8-halogenoalkylcarbonyl; arylcarbonyl; C3-C8-cycloalkylcarbonyl; C3-C8-halogenocycloalkylcarbonyl; C1-C8-alkylcarbamoyl; di-C1-C8-alkylcarbamoyl; N-C1-C8-alkyloxycarbamoyl; C1-C8-alkoxycarbamoyl; N-C1-C8-alkyl-C1-C8-alkoxycarbamoyl; C1-C8-alkoxycarbonyl; C1-C8-halogenoalkoxycarbonyl; C3-C8-cycloalkoxycarbonyl; C2-C8-alkoxyalkylcarbonyl; C2-C8-halogenoalkoxyalkylcarbonyl; C3-C10-cycloalkoxyalkylcarbonyl; C1-C8-alkylaminocarbonyl; di-C1-C8-alkylaminocarbonyl; C3-C8-cycloalkylaminocarbonyl; C1-C8-alkylcarbonyloxy; C1-C8-halogenoalkylcarbonyloxy; C3-C8-cycloalkylcarbonyloxy; C1-C8-alkylcarbonylamino; C1-C8-halogenoalkylcarbonylamino; C1-C8-alkylaminocarbonyloxy; di-C1-C8-alkylaminocarbonyloxy; C1-C8-alkyloxycarbonyloxy; C1-C8-alkylsulfinyl; C1-C8-halogenoalkylsulfinyl; C1-C8-alkylsulfonyl; C1-C8-halogenoalkylsulfonyl; C1-C8-alkylsulfonyloxy; C1-C8-halogenoalkylsulfonyloxy; C1-C8-alkylaminosulfamoyl; di-C1-C8-alkylaminosulfamoyl; (C1-C8-alkoxyimino)-C1-C8-alkyl; (C3-C7-cycloalkoxyimino)-C1-C8-alkyl; hydroxyimino-C1-C8-alkyl; (C1-C8-alkoxyimino)-C3-C7-cycloalkyl; hydroxyimino-C3-C7-cycloalkyl; (C1-C8-alkylimino)-oxy; (C1-C8-alkylimino)-oxy-C1-C8-alkyl; (C3-C7-cycloalkylimino)-oxy-C1-C8-alkyl; (C1-C6-alkylimino)-oxy-C3-C7-cycloalkyl; (C1-C8-alkenyloxyimino)-C1-C8-alkyl; (C1-C8-alkynyloxyimino)-C1-C8-alkyl; (benzyloxyimino)-C1-Cs-alkyl; C1-C8-alkoxyalkyl; C1-C8-alkylthioalkyl; C1-C8-alkoxyalkoxyalkyl; C1-C8-halogenoalkoxyalkyl; benzyl; phenyl; 5-membered heteroaryl; 6-membered heteroaryl; benzyloxy; phenyloxy; benzylsulfanyl; benzylamino; phenylsulfanyl; or phenylamino;
R2 represents H, C1-C8-alkyl, -Si(R3a)(R3b)(R3c), -P(O)(OH)2, -CH2-O-P(O)(OH)2, C(O)-C1-C8-alkyl, -C(O)-C3-C7-cycloalkyl, -C(O)NH-C1-C8-alkyl; -C(O)N-di-C1-C8-alkyl; -C(O)O-C1-C8-alkyl; wherein the -C(O)-C1-C8-alkyl, -C(O)-C3-C7-cycloalkyl, C(O)NH-C1-C8-alkyl; -C(O)N-di-C1-C8-alkyl or -C(O)O-C1-C8-alkyl may be non-substituted or substituted by one or more group(s) selected from
halogen or C1-C8-alkoxy;
wherein
R3a, R3b, R3c represent independent from each other a phenyl or C1-C8-alkyl;
Q represents a substituted 6-membered aromatic heterocycle of formula (Q-I) containing one nitrogen atom
U1 represents CX1 or N;
wherein X1 represents hydrogen, halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-alkoxy; or C1-C8-halogenalkyloxy;
U2 represents CX2 or N;
wherein X2 represents hydrogen, halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-alkoxy; or C1-C8-halogenalkyloxy;
U3 represents CX3 or N;
wherein X3 represents hydrogen, halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-alkoxy; or C1-C8-halogenalkyloxy;
U4 represents CX4 or N;
wherein X4 represents hydrogen, halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-alkoxy; or C1-C8-halogenalkyloxy;
U5 represents CX5 or N; wherein X5 represents hydrogen, halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-alkoxy; or C1-C8-halogenalkyloxy;
and wherein one of U1, U2, U3, U4 or U5 represents N and wherein at least one of X1, X2, X3, X4 or X5 is different from hydrogen;R1 represents non-substituted phenyl or phenyl which is substituted by one or more group(s) selected from halogen; hydroxyl; cyano; amino; sulfanyl; pentafluoro-λ6-sulfanyl; carboxaldehyde, hydroxycarbonyl, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-cyanoalkyl; C1-C8-alkyloxy; C1-C8-halogenalkyloxy; tri(C1-C8-alkyl)silyl; tri(C1-C8-alkyl)silyl-C1-C8-alkyl; C3-C7-cycloalkyl; C3-C7-halogencycloalkyl; C3-C7-cycloalkenyl; C3-C7-halogencycloalkenyl; C4-C10-cycloalkylalkyl; C4-C10-halocycloalkylalkyl; C6-C12-cycloalkylcycloalkyl; C1-C8-alkyl-C3-C7-cycloalkyl; C1-C8-alkoxy-C3-C7-cycloalkyl; tri(C1-C8-alkyl)silyl-C3-C7-cycloalkyl; C2-C8-alkenyl; C2-C8-alkynyl; C2-C8-alkenyloxy; C2-C8-halogenalkenyloxy; C3-C8-alkynyloxy; C3-C8-halogenoalkynyloxy; C1-C8-alkylamino; C1-C8-halogenalkylamino; C1-C8-cyanoalkoxy; C4-C8-cycloalkylalkoxy; C3-C6-cycloalkoxy; C1-C8-alkylsulfanyl; C1-Cs-halogenoalkylsulfanyl; C1-C8-alkylcarbonyl; C1-C8-halogenoalkylcarbonyl; arylcarbonyl; C3-C8-cycloalkylcarbonyl; C3-C8-halogenocycloalkylcarbonyl; C1-C8-alkylcarbamoyl; di-C1-Cs-alkylcarbamoyl; N-C1-C8-alkyloxycarbamoyl; C1-C8-alkoxycarbamoyl; N-C1-C8-alkyl-C1-C8-alkoxycarbamoyl; C1-C8-alkoxycarbonyl; C1-C8-halogenoalkoxycarbonyl; C3-C8-cycloalkoxycarbonyl; C2-C8-alkoxyalkylcarbonyl; C2-C8-halogenoalkoxyalkylcarbonyl; C3-C10-cycloalkoxyalkylcarbonyl; C1-C8-alkylaminocarbonyl; di-C1-C8-alkylaminocarbonyl; C3-C8-cycloalkylaminocarbonyl; C1-C8-alkylcarbonyloxy; C1-C8-halogenoalkylcarbonyloxy; C3-C8-cycloalkylcarbonyloxy; C1-C8-alkylcarbonylamino; C1-C8-halogenoalkylcarbonylamino; C1-C8-alkylaminocarbonyloxy; di-C1-C8-alkylaminocarbonyloxy; C1-C8-alkyloxycarbonyloxy; C1-C8-alkylsulfinyl; C1-C8-halogenoalkylsulfinyl; C1-C8-alkylsulfonyl; C1-C8-halogenoalkylsulfonyl; C1-C8-alkylsulfonyloxy; C1-C8-halogenoalkylsulfonyloxy; Ci-Cs-alkylaminosulfamoyl; di-C1-C8-alkylaminosulfamoyl; (C1-C8-alkoxyimino)-C1-C8-alkyl; (C3-C7-cycloalkoxyimino)-C1-C8-alkyl; hydroxyimino-C1-C8-alkyl; (C1-C8-alkoxyimino)-C3-C7-cycloalkyl; hydroxyimino-C3-C7-cycloalkyl; (C1-C8-alkylimino)-oxy; (C1-C8-alkylimino)-oxy-C1-C8-alkyl; (C3-C7-cycloalkylimino)-oxy-C1-C8-alkyl; (C1-C6-alkylimino)-oxy-C3-C7-cycloalkyl; (C1-C8-alkenyloxyimino)-C1-C8-alkyl; (C1-C8-alkynyloxyimino)-C1-C8-alkyl; (benzyloxyimino)-C1-C8-alkyl; C1-C8-alkoxyalkyl; C1-C8-alkylthioalkyl; C1-C8-alkoxyalkoxyalkyl; C1-C8-halogenoalkoxyalkyl; benzyl; phenyl; 5-membered heteroaryl; 6-membered heteroaryl; benzyloxy; phenyloxy; benzylsulfanyl; benzylamino; phenylsulfanyl; or phenylamino;
R2 represents H, C1-C8-alkyl, halogen- or C1-C8-alkoxy-substituted or non-substituted -C(O)-C1-C8-alkyl;
and wherein Q has the same meaning as given in claim 1.R1 represents non-substituted phenyl or phenyl which is substituted by one or more group(s) selected from halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-halogenalkyloxy; C3-C7-cycloalkyl; C2-C8-alkenyl; C2-C8-alkynyl; C2-C8-alkenyloxy; C3-C8-alkynyloxy; C3-C8-halogenoalkynyloxy; C1-C8-alkoxy; phenyl; 5-membered heteroaryl; 6-membered heteroaryl; benzyloxy; phenyloxy; benzylsulfanyl; benzylamino; phenylsulfanyl; or phenylamino; wherein the benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy or phenyloxy may be optionally substituted by one or more group(s) selected from halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-halogenalkyloxy; C3-C7-cycloalkyl; C2-C8-alkenyl; C2-C8-alkynyl; C2-C8-alkenyloxy; C3-C8-alkynyloxy; C3-C8-halogenoalkynyloxy; C1-C8-alkoxy; phenyl; 5-membered heteroaryl; 6-membered heteroaryl; benzyloxy; phenyloxy; benzylsulfanyl; benzylamino; phenylsulfanyl; or phenylamino.
R2 represents H, C1-C8-alkyl, halogen- or C1-C8-alkoxy-substituted or non-substituted -C(O)-C1-C8-alkyl;
Q represents a substituted 6-membered aromatic heterocycle containing one nitrogen
atom of formula (Q-I-1) to (Q-I-3)
wherein X1, X2, X3, X4 or X5 independent from each other represent hydrogen, halogen, C1-C8-alkyl; C1-C8-haloalkyl; Ci-Cs-alkoxy; or C1-C8-halogenalkyloxy; preferably represent hydrogen or halogen;
and wherein at least one of X1, X2, X3, X4 or X5 is different from hydrogen; and its salts or N-oxides.
R1 represents non-substituted phenyl or phenyl which is substituted by one or more group(s) selected from halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-halogenalkyloxy; C3-C7-cycloalkyl; C2-C8-alkenyl; C2-C8-alkynyl; C2-C8-alkenyloxy; C3-C8-alkynyloxy; C3-C8-halogenoalkynyloxy; C1-C8-alkoxy; phenyl; 5-membered heteroaryl; 6-membered heteroaryl; benzyloxy; phenyloxy; benzylsulfanyl; benzylamino; phenylsulfanyl; or phenylamino; wherein the benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy or phenyloxy may be optionally substituted by one or more group(s) selected from halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-halogenalkyloxy; C3-C7-cycloalkyl; C2-C8-alkenyl; C2-C8-alkynyl; C2-C8-alkenyloxy; C3-C8-alkynyloxy; C3-C8-halogenoalkynyloxy; C1-C8-alkoxy; phenyl; 5-membered heteroaryl; 6-membered heteroaryl; benzyloxy; phenyloxy; benzylsulfanyl; benzylamino; phenylsulfanyl; or phenylamino.
R2 represents H, C1-C8-alkyl, halogen- or C1-C8-alkoxy-substituted or non-substituted -C(O)-C1-C8-alkyl;
Q represents a substituted 6-membered aromatic heterocycle containing one nitrogen
atom of formula (Q-I-1) to (Q-I-2)
wherein X1, X2, X3, X4 or X5 independent from each other represent hydrogen, halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-alkoxy; or C1-C8-halogenalkyloxy; preferably represent hydrogen or halogen;
and wherein at least one of X1, X2, X3, X4 or X5 is different from hydrogen;
Q represents a substituted 6-membered aromatic heterocycle of formula (Q-I) containing
one nitrogen atom
U1 represents CX1 or N;
wherein X1 represents hydrogen, halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-alkoxy; or C1-C8-halogenalkyloxy;
U2 represents CX2 or N;
wherein X2 represents hydrogen, halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-alkoxy; or C1-C8-halogenalkyloxy;
U3 represents CX3 or N;
wherein X3 represents hydrogen, halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-alkoxy; or C1-C8-halogenalkyloxy;
U4 represents CX4 or N;
wherein X4 represents hydrogen, halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-alkoxy; or C1-C8-halogenalkyloxy;
U5 represents CX5 or N;
wherein X5 represents hydrogen, halogen, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-alkoxy; or C1-C8-halogenalkyloxy;
R1 represents phenyl or naphthyl; wherein the phenyl or naphthyl may be non-substituted or substituted by one or more group(s) selected from halogen; hydroxyl; cyano; amino; sulfanyl; pentafluoro-λ6-sulfanyl; carboxaldehyde, hydroxycarbonyl, C1-C8-alkyl; C1-C8-haloalkyl; C1-C8-cyanoalkyl; C1-C8-alkyloxy; C1-C8-halogenalkyloxy; tri(C1-C8-alkyl)silyl; tri(C1-C8-alkyl)silyl-C1-C8-alkyl; C3-C7-cycloalkyl; C3-C7-halogencycloalkyl; C3-C7-cycloalkenyl; C3-C7-halogencycloalkenyl; C4-C10-cycloalkylalkyl; C4-C10-halocycloalkylalkyl; C6-C12-cycloalkylcycloalkyl; C1-C8-alkyl-C3-C7-cycloalkyl; C1-C8-alkoxy-C3-C7-cycloalkyl; tri(C1-C8-alkyl)silyl-C3-C7-cycloalkyl; C2-C8-alkenyl; C2-C8-alkynyl; C2-C8-alkenyloxy; C2-C8-halogenalkenyloxy; C3-C8-alkynyloxy; C3-C8-halogenoalkynyloxy; C1-C8-alkylamino; C1-C8-halogenalkylamino; C1-C8-cyanoalkoxy; C4-C8-cycloalkylalkoxy; C3-C6-cycloalkoxy; C1-C8-alkylsulfanyl; C1-C8-halogenoalkylsulfanyl; C1-C8-alkylcarbonyl; C1-C8-halogenoalkylcarbonyl; arylcarbonyl; C3-C8-cycloalkylcarbonyl; C3-C8-halogenocycloalkylcarbonyl; C1-C8-alkylcarbamoyl; di-C1-C8-alkylcarbamoyl; N-C1-C8-alkyloxycarbamoyl; C1-C8-alkoxycarbamoyl; N-C1-C8-alkyl-C1-C8-alkoxycarbamoyl; C1-C8-alkoxycarbonyl; C1-C8-halogenoalkoxycarbonyl; C3-C8-cycloalkoxycarbonyl; C2-C8-alkoxyalkylcarbonyl; C2-C8-halogenoalkoxyalkylcarbonyl; C3-C10-cycloalkoxyalkylcarbonyl; C1-C8-alkylaminocarbonyl; di-C1-C8-alkylaminocarbonyl; C3-C8-cycloalkylaminocarbonyl; C1-C8-alkylcarbonyloxy; C1-C8-halogenoalkylcarbonyloxy; C3-C8-cycloalkylcarbonyloxy; C1-C8-alkylcarbonylamino; C1-C8-halogenoalkylcarbonylamino; C1-C8-alkylaminocarbonyloxy; di-C1-C8-alkylaminocarbonyloxy; C1-C8-alkyloxycarbonyloxy; C1-C8-alkylsulfinyl; C1-C8-halogenoalkylsulfinyl; C1-C8-alkylsulfonyl; C1-C8-halogenoalkylsulfonyl; C1-C8-alkylsulfonyloxy; C1-C8-halogenoalkylsulfonyloxy; C1-C8-alkylaminosulfamoyl; di-C1-C8-alkylaminosulfamoyl; (C1-C8-alkoxyimino)-C1-C8-alkyl; (C3-C7-cycloalkoxyimino)-C1-C8-alkyl; hydroxyimino-C1-C8-alkyl; (C1-C8-alkoxyimino)-C3-C7-cycloalkyl; hydroxyimino-C3-C7-cycloalkyl; (C1-C8-alkylimino)-oxy; (C1-C8-alkylimino)-oxy-C1-C8-alkyl; (C3-C7-cycloalkylimino)-oxy-C1-C8-alkyl; (C1-C6-alkylimino)-oxy-C3-C7-cycloalkyl; (C1-C8-alkenyloxyimino)-C1-C8-alkyl; (C1-C8-alkynyloxyimino)-C1-C8-alkyl; (benzyloxyimino)-C1-C8-alkyl; C1-C8-alkoxyalkyl; C1-C8-alkylthioalkyl; C1-C8-alkoxyalkoxyalkyl; C1-C8-halogenoalkoxyalkyl; benzyl; phenyl; 5-membered heteroaryl; 6-membered heteroaryl; benzyloxy; phenyloxy; benzylsulfanyl; benzylamino; phenylsulfanyl; or phenylamino;
and its salts or N-oxides.R1 für Phenyl oder Naphthyl steht, wobei Phenyl bzw. Naphthyl unsubstituiert oder durch eine oder mehrere Gruppen ausgewählt aus Halogen, Hydroxyl, Cyano, Amino, Sulfanyl, Pentafluor-λ6-sulfanyl, Carboxaldehyd, Hydroxycarbonyl, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Cyanoalkyl, C1-C8-Alkyloxy, C1-C8-Halogenalkyloxy, Tri(C1-C8-alkyl) silyl, Tri(C1-C8-alkyl)silyl-C1-C8-alkyl, C3-C7-Cycloalkyl, C3-C7-Halogencycloalkyl, C3-C7-Cycloalkenyl, C3-C7-Halogencycloalkenyl, C4-C10-Cycloalkylalkyl, C4-C10-Halogencycloalkylalkyl, C6-C12-Cycloalkylcycloalkyl, C1-C8-Alkyl-C3-C7-cycloalkyl, C1-C8-Alkoxy-C3-C7-cycloalkyl, Tri (C1-C8-alkyl) silyl-C3-C7-cycloalkyl, C2-C8-Alkenyl, C2-C8-Alkinyl, C2-C8-Alkenyloxy, C2-C8-Halogenalkenyloxy, C3-C8-Alkinyloxy, C3-C8-Halogenalkinyloxy, C1-C8-Alkylamino, C1-C8-Halogenalkylamino, C1-C8-Cyanoalkoxy, C4-C8-Cycloalkylalkoxy, C3-C6-Cycloalkoxy, C1-C8-Alkylsulfanyl, C1-C8-Halogenalkylsulfanyl, C1-C8-Alkylcarbonyl, C1-C8-Halogenalkylcarbonyl, Arylcarbonyl, C3-C8-Cycloalkylcarbonyl, C3-C8-Halogencycloalkylcarbonyl, C1-C8-Alkylcarbamoyl, Di-C1-C8-alkylcarbamoyl, N-C1-C8-Alkyloxy-carbamoyl, C1-C8-Alkoxycarbamoyl, N-C1-C8-Alkyl-C1-C8-alkoxycarbamoyl, C1-C8-Alkoxycarbonyl, C1-C8-Halogenalkoxycarbonyl, C3-C8-Cycloalkoxycarbonyl, C2-C8-Alkoxyalkylcarbonyl, C2-C8-Halogenalkoxyalkylcarbonyl, C3-C10-Cycloalkoxyalkylcarbonyl, C1-C8-Alkylaminocarbonyl, Di-C1-C8-alkylaminocarbonyl, C3-C8-Cycloalkylaminocarbonyl, C1-C8-Alkylcarbonyloxy, C1-C8-Halogenalkylcarbonyloxy, C3-C8-Cycloalkylcarbonyloxy, C1-C8-Alkylcarbonylamino, C1-C8-Halogenalkylcarbonylamino, C1-C8-Alkylaminocarbonyloxy, Di-C1-C8-alkylaminocarbonyloxy, C1-C8-Alkyloxycarbonyloxy, C1-C8-Alkylsulfinyl, C1-C8-Halogenalkylsulfinyl, C1-C8-Alkylsulfonyl, C1-C8-Halogenalkylsulfonyl, C1-C8-Alkylsulfonyloxy, C1-C8-Halogenalkylsulfonyloxy, C1-C8-Alkylaminosulfamoyl, Di-C1-C8-alkylaminosulfamoyl, (C1-C8-Alkoxyimino)-C1-C8-alkyl, (C3-C7-Cycloalkoxyimino)-C1-C8-alkyl, Hydroxyimino-C1-C8-alkyl, (C1-C8-Alkoxyimino)-C3-C7-cycloalkyl, Hydroxyimino-C3-C7-cycloalkyl, (C1-C8-Alkylimino)oxy, (C1-C8-Alkylimino)oxy-C1-C8-alkyl, (C3-C7-Cycloalkylimino)oxy-C1-C8-alkyl, (C1-C6-Alkylimino)-oxy-C3-C7-cycloalkyl, (C1-C8-Alkenyloxyimino)-C1-C8-alkyl, (C1-C8-Alkinyloxyimino)-C1-C8-alkyl, (Benzyloxyimino)-C1-C8-alkyl, C1-C8-Alkoxyalkyl, C1-C8-Alkylthioalkyl, C1-C8-Alkoxyalkoxyalkyl, C1-C8-Halogenalkoxyalkyl, Benzyl, Phenyl, 5-gliedrigem Heteroaryl, 6-gliedrigem Heteroaryl, Benzyloxy, Phenyloxy, Benzylsulfanyl, Benzylamino, Phenylsulfanyl und Phenylamino substituiert sein kann,
R2 für H, C1-C8-Alkyl, -Si(R3a)(R3b)(R3c), -P(O)(OH)2, -CH2-O-P(O)(OH)2, -C(O)-C1-C8-Alkyl, -C(O)-C3-C7-Cycloalkyl, -C(O)NH-C1-C8-Alkyl, -C(O)N-Di-C1-C8-alkyl, -C(O)O-C1-C8-Alkyl steht, wobei -C(O)-C1-C8-Alkyl, -C(O)-C3-C7-Cycloalkyl, -C(O)NH-C1-C8-Alkyl, -C(O)N-Di-C1-C8-alkyl oder -C(O)O-C1-C8-Alkyl unsubstituiert oder durch eine oder mehrere aus Halogen und C1-C8-Alkoxy ausgewählte Gruppen substituiert sein können,
wobei R3a, R3b, R3c unabhängig voneinander für Phenyl oder C1-C8-Alkyl stehen,
Q für einen substituierten 6-gliedrigen aromatischen Heterocyclus der Formel (Q-I)
mit einem Stickstoffatom steht
U1 für CX1 oder N steht, wobei X1 für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy oder C1-C8-Halogenalkyloxy steht,
U2 für CX2 oder N steht,
wobei X2 für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy oder C1-C8-Halogenalkyloxy steht,
U3 für CX3 oder N steht,
wobei X3 für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy oder C1-C8-Halogenalkyloxy steht,
U4 für CX4 oder N steht,
wobei X4 für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy oder C1-C8-Halogenalkyloxy steht,
U5 für CX5 oder N steht,
wobei X5 für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy oder C1-C8-Halogenalkyloxy steht,
R1 für unsubstituiertes Phenyl oder Phenyl, welches durch eine oder mehrere Gruppen ausgewählt aus Halogen, Hydroxyl, Cyano, Amino, Sulfanyl, Pentafluor-λ6-sulfanyl, Carboxaldehyd, Hydroxycarbonyl, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Cyanoalkyl, C1-C8-Alkyloxy, C1-C8-Halogenalkyloxy, Tri(C1-C8-alkyl)silyl, Tri(C1-C8-alkyl)silyl-C1-C8-alkyl, C3-C7-Cycloalkyl, C3-C7-Halogencycloalkyl, C3-C7-Cycloalkenyl, C3-C7-Halogencycloalkenyl, C4-C10-Cycloalkylalkyl, C4-C10-Halogencycloalkylalkyl, C6-C12-Cycloalkylcycloalkyl, C1-C8-Alkyl-C3-C7-cycloalkyl, C1-C8-Alkoxy-C3-C7-cycloalkyl, Tri(C1-C8-alkyl)silyl-C3-C7-cycloalkyl, C2-C8-Alkenyl, C2-C8-Alkinyl, C2-C8-Alkenyloxy, C2-C8-Halogenalkenyloxy, C3-C8-Alkinyloxy, C3-C8-Halogenalkinyloxy, C1-C8-Alkylamino, C1-C8-Halogenalkylamino, C1-C8-Cyanoalkoxy, C4-C8-Cycloalkylalkoxy, C3-C6-Cycloalkoxy, C1-C8-Alkylsulfanyl, C1-C8-Halogenalkylsulfanyl, C1-C8-Alkylcarbonyl, C1-C8-Halogenalkylcarbonyl, Arylcarbonyl, C3-C8-Cycloalkylcarbonyl, C3-C8-Halogencycloalkylcarbonyl, C1-C8-Alkylcarbamoyl, Di-C1-C8-alkylcarbamoyl, N-C1-C8-Alkyloxycarbamoyl, C1-C8-Alkoxycarbamoyl, N-C1-C8-Alkyl-C1-C8-alkoxycarbamoyl, C1-C8-Alkoxycarbonyl, C1-C8-Halogenalkoxycarbonyl, C3-C8-Cycloalkoxycarbonyl, C2-C8-Alkoxyalkylcarbonyl, C2-C8-Halogenalkoxyalkylcarbonyl, C3-C10-Cycloalkoxyalkylcarbonyl, C1-C8-Alkylaminocarbonyl, Di-C1-C8-alkylaminocarbonyl, C3-C8-Cycloalkylaminocarbonyl, C1-C8-Alkylcarbonyloxy, C1-C8-Halogenalkylcarbonyloxy, C3-C8-Cycloalkylcarbonyloxy, C1-C8-Alkylcarbonylamino, C1-C8-Halogenalkylcarbonylamino, C1-C8-Alkylaminocarbonyloxy, Di-C1-C8-alkylaminocarbonyloxy, C1-C8-Alkyloxycarbonyloxy, C1-C8-Alkylsulfinyl, C1-C8-Halogenalkylsulfinyl, C1-C8-Alkylsulfonyl, C1-C8-Halogenalkylsulfonyl, C1-C8-Alkylsulfonyloxy, C1-C8-Halogenalkylsulfonyloxy, C1-C8-Alkylaminosulfamoyl, Di-C1-C8-alkylaminosulfamoyl, (C1-C8-Alkoxyimino)-C1-C8-alkyl, (C3-C7-Cycloalkoxyimino) -C1-C8-alkyl, Hydroxyimino-C1-C8-alkyl, (C1-C8-Alkoxyimino)-C3-C7-cycloalkyl, Hydroxyimino-C3-C7-cycloalkyl, (C1-C8-Alkylimino)oxy, (C1-C8-Alkylimino) oxy-C1-C8-alkyl, (C3-C7-Cycloalkylimino) oxy-C1-C8-alkyl, (C1-C6-Alkylimino) oxy-C3-C7-cycloalkyl, (C1-C8-Alkenyloxyimino)-C1-C8-alkyl, (C1-C8-Alkinyloxyimino)-C1-C8-alkyl, (Benzyloxyimino)-C1-C8-alkyl, C1-C8-Alkoxyalkyl, C1-C8-Alkylthioalkyl, C1-C8-Alkoxyalkoxyalkyl, C1-C8-Halogenalkoxyalkyl, Benzyl, Phenyl, 5-gliedrigem Heteroaryl, 6-gliedrigem Heteroaryl, Benzyloxy, Phenyloxy, Benzylsulfanyl, Benzylamino, Phenylsulfanyl und Phenylamino substituiert ist, steht,
R2 für H, C1-C8-Alkyl, Halogen- oder C1-C8-Alkoxy-substituiertes oder unsubstituiertes-C(O)-C1-C8-Alkyl steht,
und wobei Q die gleiche Bedeutung wie nach Anspruch 1 hat,R1 für unsubstituiertes Phenyl oder Phenyl, das durch eine oder mehrere Gruppen ausgewählt aus Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl,C1-C8-Halogenalkyloxy, C3-C7-Cycloalkyl, C2-C8-Alkenyl, C2-C8-Alkinyl, C2-C8-Alkenyloxy, C3-C8-Alkinyloxy, C3-C8-Halogenalkinyloxy, C1-C8-Alkoxy, Phenyl, 5-gliedrigem Heteroaryl, 6-gliedrigem Heteroaryl, Benzyloxy, Phenyloxy, Benzylsulfanyl, Benzylamino, Phenylsulfanyl und Phenylamino substituiert ist, steht, wobei Benzyl, Phenyl, 5-gliedriges Heteroaryl, 6-gliedriges Heteroaryl, Benzyloxy und Phenyloxy gegebenenfalls durch eine oder mehrere Gruppen ausgewählt aus Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl,C1-C8-Halogenalkyloxy, C3-C7-Cycloalkyl, C2-C8-Alkenyl, C2-C8-Alkinyl, C2-C8-Alkenyloxy, C3-C8-Alkinyloxy, C3-C8-Halogenalkinyloxy, C1-C8-Alkoxy, Phenyl, 5-gliedrigem Heteroaryl, 6-gliedrigem Heteroaryl, Benzyloxy, Phenyloxy, Benzylsulfanyl, Benzylamino, Phenylsulfanyl und Phenylamino substituiert sein können,
R2 für H, C1-C8-Alkyl, Halogen- oder C1-C8-Alkoxy-substituiertes oder unsubstituiertes-C(O)-C1-C8-Alkyl steht,
Q für einen substituierten 6-gliedrigen aromatischen Heterocyclus mit einem Stickstoffatom
der Formel (Q-I-1) bis (Q-I-3) steht
wobei X1, X2, X3, X4 und X5 unabhängig voneinander jeweils für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy oder C1-C8-Halogenalkyloxy stehen und vorzugsweise für Wasserstoff oder Halogen stehen,
und wobei mindestens einer der Reste X1, X2, X3, X4 und X5 von Wasserstoff verschieden ist,
R1 für unsubstituiertes Phenyl oder Phenyl, das durch eine oder mehrere Gruppen ausgewählt aus Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Halogenalkyloxy, C3-C7-Cycloalkyl, C2-C8-Alkenyl, C2-C8-Alkinyl, C2-C8-Alkenyloxy, C3-C8-Alkinyloxy, C3-C8-Halogenalkinyloxy, C1-C8-Alkoxy, Phenyl, 5-gliedrigem Heteroaryl, 6-gliedrigem Heteroaryl, Benzyloxy, Phenyloxy, Benzylsulfanyl, Benzylamino, Phenylsulfanyl und Phenylamino substituiert ist, steht, wobei Benzyl, Phenyl, 5-gliedriges Heteroaryl, 6-gliedriges Heteroaryl, Benzyloxy und Phenyloxy gegebenenfalls durch eine oder mehrere Gruppen ausgewählt aus Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Halogenalkyloxy, C3-C7-Cycloalkyl, C2-C8-Alkenyl, C2-C8-Alkinyl, C2-C8-Alkenyloxy, C3-C8-Alkinyloxy, C3-C8-Halogenalkinyloxy, C1-C8-Alkoxy, Phenyl, 5-gliedrigem Heteroaryl, 6-gliedrigem Heteroaryl, Benzyloxy, Phenyloxy, Benzylsulfanyl, Benzylamino, Phenylsulfanyl und Phenylamino substituiert sein können,
R2 für H, C1-C8-Alkyl, Halogen- oder C1-C8-Alkoxy-substituiertes oder unsubstituiertes-C(O)-C1-C8-Alkyl steht,
Q für einen substituierten 6-gliedrigen aromatischen Heterocyclus mit einem Stickstoffatom
der Formel (Q-I-1) bis (Q-I-2) steht
wobei X1, X2, X3, X4 und X5 unabhängig voneinander jeweils für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl,C1-C8-Alkoxy oder C1-C8-Halogenalkyloxy stehen und vorzugsweise für Wasserstoff oder Halogen stehen,
und wobei mindestens einer der Reste X1, X2, X3, X4 und X5 von Wasserstoff verschieden ist,
U1 für CX1 oder N steht,
wobei X1 für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy oder C1-C8-Halogenalkyloxy steht,
U2 für CX2 oder N steht,
wobei X2 für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy oder C1-C8-Halogenalkyloxy steht,
U3 für CX3 oder N steht,
wobei X3 für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy oder C1-C8-Halogenalkyloxy steht,
U4 für CX4 oder N steht,
wobei X4 für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy oder C1-C8-Halogenalkyloxy steht,
U5 für CX5 oder N steht,
wobei X5 für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy oder C1-C8-Halogenalkyloxy steht,
und wobei einer der Reste U1, U2, U3, U4 oder U5 für N steht und wobei mindestens einer der Reste X1, X2, X3, X4 oder X5 von Wasserstoff verschieden ist, und
R1 für Phenyl oder Naphthyl steht, wobei Phenyl bzw. Naphthyl unsubstituiert oder durch eine oder mehrere Gruppen ausgewählt aus Halogen, Hydroxyl, Cyano, Amino, Sulfanyl, Pentafluor-λ6-sulfanyl, Carboxaldehyd, Hydroxycarbonyl, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Cyanoalkyl, C1-C8-Alkyloxy, C1-C8-Halogenalkyloxy, Tri(C1-C8-alkyl)silyl, Tri(C1-C8-alkyl)silyl-C1-C8-alkyl, C3-C7-Cycloalkyl, C3-C7-Halogencycloalkyl, C3-C7-Cycloalkenyl, C3-C7-Halogencycloalkenyl, C4-C10-Cycloalkylalkyl, C4-C10-Halogencycloalkylalkyl, C6-C12-Cycloalkylcycloalkyl, C1-C8-Alkyl-C3-C7-cycloalkyl, C1-C8-Alkoxy-C3-C7-cycloalkyl, Tri (C1-C8-alkyl) silyl-C3-C7-cycloalkyl, C2-C8-Alkenyl, C2-C8-Alkinyl, C2-C8-Alkenyloxy, C2-C8-Halogenalkenyloxy, C3-C8-Alkinyloxy, C3-C8-Halogenalkinyloxy, C1-C8-Alkylamino, C1-C8-Halogenalkylamino, C1-C8-Cyanoalkoxy, C4-C8-Cycloalkylalkoxy, C3-C6-Cycloalkoxy, C1-C8-Alkylsulfanyl, C1-C8-Halogenalkylsulfanyl, C1-C8-Alkylcarbonyl, C1-C8-Halogenalkylcarbonyl, Arylcarbonyl, C3-C8-Cycloalkylcarbonyl, C3-C8-Halogencycloalkylcarbonyl, C1-C8-Alkylcarbamoyl, Di-C1-C8-alkylcarbamoyl, N-C1-C8-Alkyloxycarbamoyl, C1-C8-Alkoxycarbamoyl, N-C1-C8-Alkyl-C1-C8-alkoxycarbamoyl, C1-C8-Alkoxycarbonyl, C1-C8-Halogenalkoxycarbonyl, C3-C8-Cycloalkoxycarbonyl, C2-C8-Alkoxyalkylcarbonyl, C2-C8-Halogenalkoxyalkylcarbonyl, C3-C10-cycloalkoxyalkylcarbonyl, C1-C8-Alkylaminocarbonyl, Di-C1-C8-alkylaminocarbonyl, C3-C8-Cycloalkylaminocarbonyl, C1-C8-Alkylcarbonyloxy, C1-C8-Halogenalkylcarbonyloxy, C3-C8-Cycloalkylcarbonyloxy, C1-C8-Alkylcarbonylamino, C1-C8-Halogenalkylcarbonylamino, C1-C8-Alkylaminocarbonyloxy, Di-C1-C8-alkylaminocarbonyloxy, C1-C8-Alkyloxycarbonyloxy, C1-C8-Alkylsulfinyl, C1-C8-Halogenalkylsulfinyl, C1-C8-Alkylsulfonyl, C1-C8-Halogenalkylsulfonyl, C1-C8-Alkylsulfonyloxy, C1-C8-Halogenalkylsulfonyloxy, C1-C8-Alkylaminosulfamoyl, Di-C1-C8-alkylaminosulfamoyl, (C1-C8-Alkoxyimino)-C1-C8-alkyl, (C3-C7-Cycloalkoxyimino)-C1-C8-alkyl, Hydroxyimino-C1-C8-alkyl, (C1-C8-Alkoxyimino)-C3-C7-cycloalkyl, Hydroxyimino-C3-C7-cycloalkyl, (C1-C8-Alkylimino) oxy, (C1-C8-Alkylimino) oxy-C1-C8-alkyl, (C3-C7-Cycloalkylimino) oxy-C1-C8-alkyl, (C1-C6-Alkylimino)-oxy-C3-C7-cycloalkyl, (C1-C8-Alkenyloxyimino)-C1-C8-alkyl, (C1-C8-Alkinyloxyimino) -C1-C8-alkyl, (Benzyloxyimino) -C1-C8-alkyl, C1-C8-Alkoxyalkyl, C1-C8-Alkylthioalkyl, C1-C8-Alkoxyalkoxyalkyl, C1-C8-Halogenalkoxyalkyl, Benzyl, Phenyl, 5-gliedrigem Heteroaryl, 6-gliedrigem Heteroaryl, Benzyloxy, Phenyloxy, Benzylsulfanyl, Benzylamino, Phenylsulfanyl und Phenylamino substituiert sein kann,
und deren Salze und N-Oxide.R1 représente phényle ou naphtyle ; où phényle ou naphtyle peut être non substitué ou substitué par un ou plusieurs groupements choisis parmi halogène ; hydroxyle ; cyano ; amino ; sulfanyle ; pentafluoro-λ6-sulfanyle ; carboxaldéhyde, hydroxycarbonyle, C1-C8-alkyle ; C1-C8-halogénoalkyle ; C1-C8-cyanoalkyle ; C1-C8-alkyloxy ; C1-C8-halogénoalkyloxy ; tri (C1-C8-alkyl)silyle ; tri (C1-C8-alkyl) silyl-C1-C8-alkyle ; C3-C7-cycloalkyle ; C3-C7-halogénocycloalkyle ; C3-C7-cycloalcényle ; C3-C7-halogénocycloalcényle ; C4-C10-cycloalkylalkyle ; C4-C10-halogénocycloalkylalkyle ; C6-C12-cycloalkylcycloalkyle ; C1-C8-alkyl-C3-C7-cycloalkyle ; C1-C8-alcoxy-C3-C7-cycloalkyle ; tri(C1-C8-alkyl) silyl-C3-C7-cycloalkyle ; C2-C8-alcényle ; C2-C8-alcynyle ; C2-C8-alcényloxy ; C2-C8-halogénoalcényloxy ; C3-C8-alcynyloxy ; C3-C8-halogénoalcynyloxy ; C1-C8-alkylamino ; C1-C8-halogénoalkylamino ; C1-C8-cyanoalcoxy ; C4-C8-cycloalkylalcoxy ; C3-C6-cycloalcoxy ; C1-C8-alkylsulfanyle ; C1-C8-halogénoalkylsulfanyle ; C1-C8-alkylcarbonyle ; C1-C8-halogénoalkylcarbonyle ; arylcarbonyle ; C3-C8-cycloalkylcarbonyle ; C3-C8-halogénocycloalkylcarbonyle ; C1-C8-alkylcarbamoyle ; di-C1-C8-alkylcarbamoyle ; N-C1-C8-alkyloxycarbamoyle ; C1-C8-alcoxycarbamoyle ; N-C1-C8-alkyl-C1-C8-alcoxycarbamoyle ; C1-C8-alcoxycarbonyle ; C1-C8-halogénoalcoxycarbonyle ; C3-C8-cycloalcoxycarbonyle ; C2-C8-alcoxyalkylcarbonyle ; C2-C8-halogénoalcoxyalkylcarbonyle ; C3-C10-cycloalcoxyalkylcarbonyle ; C1-C8-alkylaminocarbonyle ; di-C1-C8-alkylaminocarbonyle ; C3-C8-cycloalkylaminocarbonyle ; C1-C8-alkylcarbonyloxy ; C1-C8-halogénoalkylcarbonyloxy ; C3-C8-cycloalkylcarbonyloxy ; C1-C8-alkylcarbonylamino ; C1-C8-halogénoalkylcarbonylamino ; C1-C8-alkylaminocarbonyloxy ; di-C1-C8-alkylaminocarbonyloxy ; C1-C8-alkyloxycarbonyloxy ; C1-C8-alkylsulfinyle ; C1-C8-halogénoalkylsulfinyle ; C1-C8-alkylsulfonyle ; C1-C8-halogénoalkylsulfonyle ; C1-C8-alkylsulfonyloxy ; C1-C8-halogénoalkylsulfonyloxy ; C1-C8-alkylaminosulfamoyle ; di-C1-C8-alkylaminosulfamoyle ; (C1-C8-alcoxyimino)-C1-C8-alkyle ; (C3-C7-cycloalcoxyimino)-C1-C8-alkyle ; hydroxyimino-C1-C8-alkyle ; (C1-C8-alcoxyimino) -C3-C7-cycloalkyle ; hydroxyimino-C3-C7-cycloalkyle ; (C1-C8-alkylimino)-oxy ; (C1-C8-alkylimino)-oxy-C1-C8-alkyle ; (C3-C7-cycloalkylimino)-oxy-C1-C8-alkyle ; (C1-C6-alkylimino)-oxy-C3-C7-cycloalkyle ; (C1-C8-alcényloxyimino)-C1-C8-alkyle ; (C1-C8-alcynyloxyimino)-C1-C8-alkyle ; (benzyloxyimino)-C1-C8-alkyle ; C1-C8-alcoxyalkyle ; C1-C8-alkylthioalkyle ; C1-C8-alcoxyalcoxyalkyle ; C1-C8-halogénoalcoxyalkyle ; benzyle ; phényle ; hétéroaryle de 5 chaînons ; hétéroaryle de 6 chaînons ; benzyloxy ; phényloxy ; benzylsulfanyle ; benzylamino ; phénylsulfanyle ; ou phénylamino ;
R2 représente H, C1-C8-alkyle, -Si(R3a)(R3b)(R3c),-P(O)(OH)2, -CH2-O-P(O)(OH)2, -C(O)-C1-C8-alkyle, -C(O)-C3-C7-cycloalkyle, -C(O)NH-C1-C8-alkyle ; -C(O)N-di-C1-C8-alkyle ; -C(O)O-C1-C8-alkyle ; où -C(O)-C1-C8-alkyle, -C(O)-C3-C7-cycloalkyle, -C(O)NH-C1-C8-alkyle ; -C(O)N-di-C1-C8-alkyle ou -C(O)O-C1-C8-alkyle peuvent être non substitués ou substitués par un ou plusieurs groupements choisis parmi halogène ou C1-C8-alcoxy ;
où R3a, R3b, R3c représentent, indépendamment les uns des autres, phényle ou C1-C8-alkyle ;
Q représente un hétérocycle aromatique de 6 chaînons substitué de formule (Q-I) contenant
un atome d'azote
U1 représente CX1 ou N ;
où X1 représente hydrogène, halogène, C1-C8-alkyle ; C1-C8-halogénoalkyle ; C1-C8-alcoxy ; ou C1-C8-halogénoalkyloxy ;
U2 représente CX2 ou N ;
où X2 représente hydrogène, halogène, C1-C8-alkyle ; C1-C8-halogénoalkyle ; C1-C8-alcoxy ; ou C1-C8-halogénoalkyloxy ;
U3 représente CX3 ou N ;
où X3 représente hydrogène, halogène, C1-C8-alkyle ; C1-C8-halogénoalkyle ; C1-C8-alcoxy ; ou C1-C8-halogénoalkyloxy ;
U4 représente CX4 ou N ;
où X4 représente hydrogène, halogène, C1-C8-alkyle ; C1-C8-halogénoalkyle ; C1-C8-alcoxy ; ou C1-C8-halogénoalkyloxy ;
U5 représente CX5 ou N ;
où X5 représente hydrogène, halogène, C1-C8-alkyle ; C1-C8-halogénoalkyle ; C1-C8-alcoxy ; ou C1-C8-halogénoalkyloxy ; et
où l'un parmi U1, U2, U3, U4 et U5 représente N et où au moins l'un parmi X1, X2, X3, X4 et X5 est autre qu'hydrogène ;
ainsi que leurs sels ou N-oxydes.U1 représente CX1 ou N ;
où X1 représente hydrogène, halogène, C1-C8-alkyle ; C1-C8-halogénoalkyle ; C1-C8-alcoxy ; ou C1-C8-halogénoalkyloxy ;
U2 représente CX2 ou N ;
où X2 représente hydrogène, halogène, C1-C8-alkyle ; C1-C8-halogénoalkyle ; C1-C8-alcoxy ; ou C1-C8-halogénoalkyloxy ;
U3 représente CX3 ou N ;
où X3 représente hydrogène, halogène, C1-C8-alkyle ; C1-C8-halogénoalkyle ; C1-C8-alcoxy ; ou C1-C8-halogénoalkyloxy ;
U4 représente CX4 ou N ;
où X4 représente hydrogène, halogène, C1-C8-alkyle ; C1-C8-halogénoalkyle ; C1-C8-alcoxy ; ou C1-C8-halogénoalkyloxy ;
U5 représente CX5 ou N ;
où X5 représente hydrogène, halogène, C1-C8-alkyle ; C1-C8-halogénoalkyle ; C1-C8-alcoxy ; ou C1-C8-halogénoalkyloxy ;
et où l'un parmi U1, U2, U3, U4 et U5 représente N et où au moins l'un parmi X1, X2, X3, X4 et X5 est autre qu'hydrogène ;
et
R1 représente phényle ou naphtyle ; où phényle ou naphtyle peut être non substitué ou substitué par un ou plusieurs groupements choisis parmi halogène ; hydroxyle ; cyano ; amino ; sulfanyle ; pentafluoro-λ6-sulfanyle ; carboxaldéhyde, hydroxycarbonyle, C1-C8-alkyle ; C1-C8-halogénoalkyle ; C1-C8-cyanoalkyle ; C1-C8-alkyloxy ; C1-C8-halogénoalkyloxy ; tri(C1-C8-alkyl)silyle ; tri (C1-C8-alkyl) silyl-C1-C8-alkyle ; C3-C7-cycloalkyle ; C3-C7-halogénocycloalkyle ; C3-C7-cycloalcényle ; C3-C7-halogénocycloalcényle ; C4-C10-cycloalkylalkyle ; C4-C10-halogénocycloalkylalkyle ; C6-C12-cycloalkylcycloalkyle ; C1-C8-alkyl-C3-C7-cycloalkyle ; C1-C8-alcoxy-C3-C7-cycloalkyle ; tri (C1-C8-alkyl) silyl-C3-C7-cycloalkyle ; C2-C8-alcényle ; C2-C8-alcynyle ; C2-C8-alcényloxy ; C2-C8-halogénoalcényloxy ; C3-C8-alcynyloxy ; C3-C8-halogénoalcynyloxy ; C1-C8-alkylamino ; C1-C8-halogénoalkylamino ; C1-C8-cyanoalcoxy ; C4-C8-cycloalkylalcoxy ; C3-C6-cycloalcoxy ; C1-C8-alkylsulfanyle ; C1-C8-halogénoalkylsulfanyle ; C1-C8-alkylcarbonyle ; C1-C8-halogénoalkylcarbonyle ; arylcarbonyle ; C3-C8-cycloalkylcarbonyle ; C3-C8-halogénocycloalkylcarbonyle ; C1-C8-alkylcarbamoyle ; di-C1-C8-alkylcarbamoyle ; N-C1-C8-alkyloxycarbamoyle ; C1-C8-alcoxycarbamoyle ; N-C1-C8-alkyl-C1-C8-alcoxycarbamoyle ; C1-C8-alcoxycarbonyle ; C1-C8-halogénoalcoxycarbonyle ; C3-C8-cycloalcoxycarbonyle ; C2-C8-alcoxyalkylcarbonyle ; C2-C8-halogénoalcoxyalkylcarbonyle ; C3-C10-cycloalcoxyalkylcarbonyle ; C1-C8-alkylaminocarbonyle ; di-C1-C8-alkylaminocarbonyle ; C3-C8-cycloalkylaminocarbonyle ; C1-C8-alkylcarbonyloxy ; C1-C8-halogénoalkylcarbonyloxy ; C3-C8-cycloalkylcarbonyloxy ; C1-C8-alkylcarbonylamino ; C1-C8-halogénoalkylcarbonylamino ; C1-C8-alkylaminocarbonyloxy ; di-C1-C8-alkylaminocarbonyloxy ; C1-C8-alkyloxycarbonyloxy ; C1-C8-alkylsulfinyle ; C1-C8-halogénoalkylsulfinyle ; C1-C8-alkylsulfonyle ; C1-C8-halogénoalkylsulfonyle ; C1-C8-alkylsulfonyloxy ; C1-C8-halogénoalkylsulfonyloxy ; C1-C8-alkylaminosulfamoyle ; di-C1-C8-alkylaminosulfamoyle ; (C1-C8-alcoxyimino)-C1-C8-alkyle ; (C3-C7-cycloalcoxyimino) -C1-C8-alkyle ; hydroxyimino-C1-C8-alkyle ; (C1-C8-alcoxyimino) -C3-C7-cycloalkyle ; hydroxyimino-C3-C7-cycloalkyle ; (C1-C8-alkylimino)-oxy ; (C1-C8-alkylimino)-oxy-C1-C8-alkyle ; (C3-C7-cycloalkylimino) -oxy-C1-C8-alkyle ; (C1-C6-alkylimino)-oxy-C3-C7-cycloalkyle ; (C1-C8-alcényloxyimino)-C1-C8-alkyle ; (C1-C8-alcynyloxyimino)-C1-C8-alkyle ; (benzyloxyimino)-C1-C8-alkyle ; C1-C8-alcoxyalkyle ; C1-C8-alkylthioalkyle ; C1-C8-alcoxyalcoxyalkyle ; C1-C8-halogénoalcoxyalkyle ; benzyle ; phényle ; hétéroaryle de 5 chaînons ; hétéroaryle de 6 chaînons ; benzyloxy ; phényloxy ; benzylsulfanyle ; benzylamino ; phénylsulfanyle ; ou phénylamino ;
ainsi que leurs sels ou N-oxydes.
REFERENCES CITED IN THE DESCRIPTION
Patent documents cited in the description
Non-patent literature cited in the description